Indazoles as hematopoietic progenitor kinase 1 (hpk1) inhibitors and methods using same

ABSTRACT

The present disclosure provides a compound of Formula (I) or pharmaceutically acceptable salts thereof, a composition comprising the compound, methods of using the compound for the treatment of various disorders associated with HPK1, and methods of preparing these compounds.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims the benefit and priority to U.S. ProvisionalPatent Application No. 63/084,059, filed on 28 Sep. 2020. The entiredisclosure of the application identified in this paragraph isincorporated herein by reference.

FIELD

The present disclosure is directed to inhibitors of hematopoieticprogenitor kinase 1 (HPK1), pharmaceutical compositions comprising theinhibitors, methods of using the inhibitors for the treatment of variousdisorders associated with HPK1, and methods of preparing thesecompounds.

BACKGROUND

Immunotherapy is treatment that uses the human body's own immune systemto help fight cancer and other disorders. This relatively new approachhas achieved remarkable clinical successes in the treatment of a varietyof tumor types in recent years, especially with the treatment of immunecheckpoint inhibitors and chimeric antigen T-cell therapy. The mostinvestigated checkpoint inhibitors including CTLA4, PD-1, or PD-L1inhibitors have demonstrated significant antitumor activity byovercoming immunosuppressive mechanisms at the tumor site.

Hematopoietic progenitor kinase 1 (HPK1, MAP4K1) is a serine/threoninekinase and a member of MAP4K. HPK1 is prominently expressed in subsetsof hematopoietic cell lineages. HPK1 is a newly identified as a criticalnegative regulator in the activation of T lymphocytes and dendriticcells. It has been recently demonstrated that the important roles forkinase activity of HPK1 in anticancer immunity as a new intracellularcheckpoint molecule as well as potential advantages of combinationtherapy with current checkpoint regimens. HPK1 inhibition is expected tohave dual functions, 1. prolonged activation of T cells; 2. enhanced APCfunctions by dendritic cells. This dual targeting may synergisticallywork together for efficient immune responses in tumor microenvironment.Thus, HPK1 has been validated as a novel target for anticancerimmunotherapy. Examples of cancers that are treatable using thecompounds of the present disclosure include, but are not limited to, allforms of carcinomas, melanomas, blastomas, sarcomas, lymphomas andleukemias, including without limitation, bladder carcinoma, braintumors, breast cancer, cervical cancer, colorectal cancer, esophagealcancer, endometrial cancer, hepatocellular carcinoma, laryngeal cancer,lung cancer, osteosarcoma, ovarian cancer, pancreatic cancer, prostatecancer, renal carcinoma and thyroid cancer, acute lymphocytic leukemia,acute myeloid leukemia, ependymoma, Ewing's sarcoma, glioblastoma,medulloblastoma, neuroblastoma, osteosarcoma, rhabdomyosarcoma, rhabdoidcancer, and nephroblastoma (Wilm's tumor).

Inhibition of HPK1 with small molecule inhibitors has the potential forthe treatment of cancer and other disorders [Hernandez, S., et. al.(2018) Cell Reports 25, 80-94].

SUMMARY

The present disclosure provides novel indazole compounds andpharmaceutically acceptable salts as effective HPK1 inhibitors and dualactivators of T cell and dendritic cell.

One embodiment of the invention is a compound represented by Formula(I):

or a pharmaceutically acceptable salt, hydrate, solvate thereof, whereinR¹, R², R³, R⁴, R⁵, Het, M, and L are as defined in the detaileddescriptions.

In another embodiment, there is provided a pharmaceutical compositioncomprising a pharmaceutically acceptable carrier or diluent and acompound of Formula (I) or a pharmaceutically acceptable salt thereof.

In yet another embodiment, there is provided a method of treating asubject with a disease or disorder associated with modulation of HPK1comprising: administering to the subject a therapeutically effectiveamount of a compound of Formula (I) or a pharmaceutically acceptablesalt thereof.

DETAILED DESCRIPTION

The following description is merely exemplary in nature and is notintended to limit the present disclosure, application, or uses.

Definitions

The generic terms used in the present disclosure are herein defined forclarity.

This specification uses the terms “substituent”, “radical”, “group”,“moiety”, and “fragment” interchangeably.

As used herein, the term “alkenyl” refers to a straight or branchedhydrocarbonyl group with at least one site of unsaturation, i.e., acarbon-carbon, sp2 double bond. In an embodiment, alkenyl has from 2 to12 carbon atoms. In some embodiments, alkenyl is a C₂-C₁₀ alkenyl groupor a C₂-C₆ alkenyl group. Examples of alkenyl group include, but are notlimited to, ethylene or vinyl (—CH═CH₂), allyl (—CH₂CH═CH₂),cyclopentenyl (—C₅H₇), and 5-hexenyl (—CH₂CH₂CH₂CH₂CH═CH₂).

As used herein, the term “alkoxy” is RO— where R is alkyl. Non-limitingexamples of alkoxy groups include methoxy, ethoxy and propoxy.

As used herein, the term “alkoxyalkyl” refers to an alkyl moietysubstituted with an alkoxy group. Examples of alkoxyalkyl groups includemethoxymethyl, methoxyethyl, methoxypropyl and ethoxyethyl.

As used herein, the term “alkoxycarbonyl” is ROC(O)—, where R is analkyl group as defined herein. In various embodiments, R is a C₁-C₁₀alkyl group or a C₁-C₆ alkyl group.

As used herein, the term “alkyl” refers to a straight or branched chainhydrocarbonyl group. In an embodiment, alkyl has from 1 to 12 carbonatoms. In some embodiments, alkyl is a C₁-C₁₀ alkyl group or a C₁-C₆alkyl group. Examples of alkyl groups include, but are not limited to,methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl,hexyl, heptyl, octyl, nonyl and decyl. “lower alkyl” means alkyl havingfrom 1 to 4 carbon atoms.

As used herein, if the term “C₁-C₆” is used, it means the number ofcarbon atoms is from 1 to 6. For example, C₁-C₆ alkyl means an alkylwhich carbon number is any integer of from 1 to 6.

As used herein, the term “alkylamino” refers to an amino groupsubstituted with one or more alkyl groups. “N-(alkyl)amino” is RNH— and“N,N-(alkyl)₂amino” is R₂N—, where the R groups are alkyl as definedherein and are the same or different. In various embodiments, R is aC₁-C₁₀ alkyl group or a C₁-C₆ alkyl group. Examples of alkylamino groupsinclude methylamino, ethylamino, propylamino, butylamino, dimethylamino,diethylamino, and methylethylamino.

As used herein, the term “alkylaminoalkyl” refers to an alkyl moietysubstituted with an alkylamino group, wherein alkylamino is as definedherein. Examples of alkylaminoakyl groups include methylaminomethyl andethylaminomethyl.

As used herein, the term “alkynyl” refers to a straight or branchedcarbon-chain group with at least one site of unsaturation, i.e., acarbon-carbon, sp triple bond. In an embodiment, alkynyl has from 2 to12 carbon atoms. In some embodiments, alkynyl is a C₂-C₁₀ alkynyl groupor a C₂-C₆alkynyl group. Examples of alkynyl groups include acetylenic(—C≡CH) and propargyl (—CH₂CE CH).

As used herein, the term “aryl” refers to any monocyclic or bicycliccarbon ring of up to 7 atoms in each ring, wherein at least one ring isaromatic, or an aromatic ring system of 5 to 14 carbon atoms whichincludes a carbocyclic aromatic group fused with a 5- or 6-memberedcycloalkyl group. Representative examples of aryl groups include, butare not limited to, phenyl, tolyl, xylyl, naphthyl, tetrahydronaphthyl,anthracenyl, fluorenyl, indenyl, azulenyl and indanyl. A carbocyclicaromatic group can be unsubstituted or optionally substituted.

As used herein, the term “cycloalkyl” is a hydrocarbyl group containingat least one saturated or partially unsaturated ring structure, andattached via a ring carbon. In various embodiments, it refers to asaturated or a partially unsaturated C₃-C₁₂cyclic moiety, examples ofwhich include cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl,cyclohexyl, cyclohexenyl, cycloheptyl and cyclooctyl. “Cycloalkyloxy” isRO—, where R is cycloalkyl.

As used herein, the terms “halogen” and “halo” refers to chloro (—Cl),bromo (—Br), fluoro (—F) or iodo (—I). “Haloalkoxy” refers to an alkoxygroup substituted with one or more halo groups and examples ofhaloalkoxy groups include, but are not limited to, —OCF₃, —OCHF₂ and—OCH₂F. “Haloalkoxyalkyl” refers to an alkyl moiety substituted with ahaloalkoxy group, wherein haloalkoxy is as defined herein. Examples ofhaloalkoxyalkyl groups include trifluoromethoxymethyl,trifluoroethoxymethyl and trifluoromethoxyethyl. “Haloalkyl” refers toan alkyl moiety substituted with one or more halo groups. Examples ofhaloalkyl groups include —CF₃ and —CHF₂.

As used herein, the term “heteroalkyl” refers to a straight- orbranched-chain alkyl group having from 2 to 14 carbons (in someembodiments, 2 to 10 carbons) in the chain, one or more of which hasbeen replaced by a heteroatom selected from S, O, P and N. Exemplaryheteroalkyls include alkyl ethers, secondary and tertiary alkyl amines,amides, alkyl sulfides, and the like.

As used herein, the term “heterocyclyl” includes the heteroaryls definedbelow and refers to a saturated or partially unsaturated monocyclic,bicyclic or tricyclic group of 2 to 14 ring-carbon atoms and, inaddition to ring-carbon atoms, 1 to 4 heteroatoms selected from P, N, Oand S. In various embodiments the heterocyclic group is attached toanother moiety through carbon or through a heteroatom, and is optionallysubstituted on carbon or a heteroatom. Examples of heterocyclyl includeazetidinyl, benzoimidazolyl, benzofuranyl, benzofurazanyl,benzopyrazolyl, benzotriazolyl, benzothiophenyl, benzoxazolyl,carbazolyl, carbolinyl, cinnolinyl, furanyl, imidazolyl, indolinyl,indolyl, indolazinyl, indazolyl, isobenzofuranyl, isoindolyl,isoquinolyl, isothiazolyl, isoxazolyl, naphthpyridinyl, oxadiazolyl,oxazolyl, oxazoline, isoxazoline, oxetanyl, pyranyl, pyrazinyl,pyrazolyl, pyridazinyl, pyridopyridinyl, pyridazinyl, pyridyl,pyrimidyl, pyrrolyl, quinazolinyl, quinolyl, quinoxalinyl,tetrahydropyranyl, tetrahydrothiopyranyl, tetrahydroisoquinolinyl,tetrazolyl, tetrazolopyridyl, thiadiazolyl, thiazolyl, thienyl,triazolyl, azetidinyl, 1,4-dioxanyl, hexahydroazepinyl, piperazinyl,piperidinyl, pyridin-2-onyl, pyrrolidinyl, morpholinyl, thiomorpholinyl,dihydrobenzoimidazolyl, dihydrobenzofuranyl, dihydrobenzothiophenyl,dihydrobenzoxazolyl, dihydrofuranyl, dihydroimidazolyl, dihydroindolyl,dihydroisooxazolyl, dihydroisothiazolyl, dihydrooxadiazolyl,dihydrooxazolyl, dihydropyrazinyl, dihydropyrazolyl, dihydropyridinyl,dihydropyrimidinyl, dihydropyrrolyl, dihydroquinolinyl,dihydrotetrazolyl, dihydrothiadiazolyl, dihydrothiazolyl,dihydrothienyl, dihydrotriazolyl, dihydroazetidinyl,methylenedioxybenzoyl, tetrahydrofuranyl, and tetrahydrothienyl, andN-oxides thereof “Heterocyclyloxy” is RO—, where R is heterocyclyl.“Heterocyclylthio” is RS—, where R is heterocyclyl.

As used herein, the term “3- or 4-membered heterocyclyl” refers to amonocyclic ring having 3 or 4 ring atoms wherein at least one ring atomis heteroatom selected from the group consisting of N, O and S.Non-limiting examples of 3- or 4-membered heterocyclyl includeaziridinyl, 2H-azirinyl, oxiranyl, thiiranyl, azetidinyl,2,3-dihyroazetyl, azetyl, 1,3-diazetidinyl, oxetanyl, 2H-oxetyl,thietanyl, and 2H-thietyl.

As used herein, the term “heteroaryl” refers to a monocyclic, bicyclicor tricyclic ring having up to 7 atoms in each ring, wherein at leastone ring is aromatic and contains from 1 to 4 heteroatoms in the ringselected from the group consisting of N, O and S. Non-limiting examplesof heteroaryl include pyridyl, thienyl, furanyl, pyrimidyl, imidazolyl,pyranyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, oxazolyl,isoxazoyl, pyrrolyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl,benzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzothienyl, indolyl,benzothiazolyl, benzooxazolyl, benzimidazolyl, isoindolyl,benzotriazolyl, purinyl, thianaphthenyl and pyrazinyl. Attachment ofheteroaryl can occur via an aromatic ring, or, if heteroaryl is bicyclicor tricyclic and one of the rings is not aromatic or contains noheteroatoms, through a non-aromatic ring or a ring containing noheteroatoms. “Heteroaryl” is also understood to include the N-oxidederivative of any nitrogen containing heteroaryl. “Heteroaryloxy” isRO—, where R is heteroaryl.

As used herein, the term “hydroxyalkoxy” refers to an alkoxy groupsubstituted with a hydroxyl group (—OH), wherein alkoxy is as definedherein. An example of hydroxyalkoxy is hydroxyethoxy.

As used herein, the term “hydroxyalkyl” refers to a linear or branchedmonovalent C₁-C₁₀ hydrocarbon group substituted with at least onehydroxy group and examples of hydroxyalkyl groups include, but are notlimited to, hydroxymethyl, hydroxyethyl, hydroxypropyl and hydroxybutyl.

As used herein, the term “pharmaceutically acceptable” means suitablefor use in pharmaceutical preparations, generally considered as safe forsuch use, officially approved by a regulatory agency of a national orstate government for such use, or being listed in the U.S. Pharmacopoeiaor other generally recognized pharmacopoeia for use in animals, and moreparticularly in humans.

As used herein, the term “pharmaceutically acceptable carrier” refers toa diluent, adjuvant, excipient, or carrier, or other ingredient which ispharmaceutically acceptable and with which a compound of the inventionis administered.

As used herein, the term “pharmaceutically acceptable salt” refers to asalt which may enhance desired pharmacological activity. Examples ofpharmaceutically acceptable salts include acid addition salts formedwith inorganic or organic acids, metal salts and amine salts. Examplesof acid addition salts formed with inorganic acids include salts withhydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid andphosphoric acid. Examples of acid addition salts formed with organicacids such as acetic acid, propionic acid, hexanoic acid, heptanoicacid, cyclopentanepropionic acid, glycolic acid, pyruvic acid, lacticacid, malonic acid, succinic acid, malic acid, maleic acid, fumaricacid, tartaric acid, citric acid, benzoic acid,o-(4-hydroxy-benzoyl)-benzoic acid, cinnamic acid, mandelic acid,methanesulfonic acid, ethanesulfonic acid, 1,2-ethanedisulfonic acid,2-hydroxyethane-sulfonic acid, benzenesulfonic acid,p-chlorobenzenesulfonic acid, 2-naphthalenesulfonic acid,p-toluenesulfonic acid, camphorsulfonic acid,4-methyl-bicyclo[2.2.2]oct-2-ene1-carboxylic acid, gluco-heptonic acid,4,4′-methylenebis(3-hydroxy-2-naphthoic) acid, 3-phenylpropionic acid,trimethyl-acetic acid, tertiary butylacetic acid, lauryl sulfuric acid,gluconic acid, glutamic acid, hydroxy-naphthoic acids, salicylic acid,stearic acid and muconic acid. Examples of metal salts include saltswith sodium, potassium, calcium, magnesium, aluminum, iron, and zincions. Examples of amine salts include salts with ammonia and organicnitrogenous bases strong enough to form salts with carboxylic acids.

As used herein, the term “substituted” means any of above groups (i.e.,alkyl, aryl, heteroaryl, heterocycle or cycloalkyl) wherein at least onehydrogen atom of the moiety being substituted is replaced with asubstituent. In one embodiment, each carbon atom of the group beingsubstituted is substituted with no more than two substituents. Inanother embodiment, each carbon atom of the group being substituted issubstituted with no more than one substituent. In the case of a ketosubstituent, two hydrogen atoms are replaced with an oxygen which isattached to the carbon via a double bond. Unless specifically defined,substituents include halo, hydroxyl, (lower) alkyl, haloalkyl, mono- ordi-alkylamino, aryl, heterocycle, —NO₂, B(OH)₂, BPin, —NR_(a)R_(b),—NR_(a)C(═O)R_(b), —NR_(a)C(═O)NR_(a)R_(b), —NR_(a)C(═O)OR_(b),—NR_(a)SO₂R_(b), —OR_(a), —CN, —C(═O)R_(a), —C(═O)OR_(a),—C(═O)NR_(a)R_(b), —OC(═O)R_(a), —OC(═O)OR_(a), —OC(═O)NR_(a)R_(b),—NR_(a)SO₂R_(b), —PO₃R_(a), —PO(OR_(a))(OR_(b)), —SO₂R_(a), —S(O)R_(a),—SO(N)R_(a) (e.g., sulfoximine), —(R_(a))S═NR_(b) (e.g., sulfilimine)and —SR_(a), wherein R_(a) and R_(b) are the same or different andindependently —H, halo, amino, alkyl, haloalkyl, aryl or heterocycle, orwherein R_(a) and R_(b) taken together with the nitrogen atom to whichthey are attached form a heterocycle. R_(a) and R_(b) may be in theplural based on atoms which those are attached to.

As used herein, the term “therapeutically effective amount” means whenapplied to a compound of the invention is intended to denote an amountof the compound that is sufficient to ameliorate, palliate, stabilize,reverse, slow or delay the progression of a disorder or disease state,or of a symptom of the disorder or disease. In an embodiment, the methodof the present invention provides for administration of combinations ofcompounds. In such instances, the “therapeutically effective amount” isthe amount of a compound of the present invention in the combinationsufficient to cause the intended biological effect.

As used herein, the term “treatment” or “treating” as used herein meansameliorating or reversing the progress or severity of a disease ordisorder, or ameliorating or reversing one or more symptoms or sideeffects of such disease or disorder. “Treatment” or “treating”, as usedherein, also means to inhibit or block, as in retard, arrest, restrain,impede or obstruct, the progress of a system, condition or state of adisease or disorder. For purposes of this invention, “treatment” or“treating” further means an approach for obtaining beneficial or desiredclinical results, where “beneficial or desired clinical results”include, without limitation, alleviation of a symptom, diminishment ofthe extent of a disorder or disease, stabilized (i.e., not worsening)disease or disorder state, delay or slowing of a disease or disorderstate, amelioration or palliation of a disease or disorder state, andremission of a disease or disorder, whether partial or total.

Compounds

The present disclosure provides a compound of Formula (I):

or a pharmaceutically acceptable salt, hydrate, or solvate, thereof,wherein:

-   X is O or S;-   L is a bond, —O—, —S—, or —NR⁶—;-   R¹ is alkyl, cycloalkyl, aryl, heteroaryl, or heterocyclyl, wherein    R¹ is optionally substituted with one or more substituents    independently selected from R⁷;-   R⁶ is —H or C₁₋₆ alkyl;-   R⁷ is C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, cycloalkyl, aryl,    heteroaryl, heterocyclyl, halo, oxo, cyano, hydroxy, —C(O)R⁹,    —C(O)OR⁹, —C(O)NR¹⁰R¹¹, —OR⁹, —OC(O)R⁹, —OC(O)NR¹⁰R¹¹, —SR⁹,    —S(O)R⁹, —S(O)₂R⁹, —S(O)(═NH)R¹⁰, —S(O)₂NR¹⁰R¹¹, —NR¹⁰R¹¹,    —N(R⁶)NR¹⁰R¹¹, —N(R⁶)OR⁹, —N(R⁶)C(O)R⁹, —N(R⁶)C(O)OR⁹,    —N(R⁶)C(O)NR¹⁰R¹¹, —N(R⁶)S(O)₂R⁹, —N(R⁶)S(O)₂NR¹⁰R¹¹, or    —P(O)R¹²R¹³;-   R⁹ is —H, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl,    cycloalkyl, aryl, heteroaryl, or heterocyclyl;-   Each R¹⁰ and R¹¹ is independently —H, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆    alkynyl, cycloalkyl, aryl, heteroaryl, or heterocyclyl, or R¹⁰ and    R¹¹ are taken together with the nitrogen atom to which they are    attached to form a 4- to 12-membered heterocyclyl optionally    substituted with one or more groups selected from the group    consisting of halo, hydroxyl, alkyl, alkenyl, alkynyl, haloalkyl,    hydroxyalkyl, —CN, —NO₂, —NR¹⁰R¹¹, —NR¹⁰C(═O)R⁹, —NR¹⁰C(═O)NR¹⁰R¹¹,    —NR¹⁰C(═O)OR⁹, —OR⁹, —C(═O)R⁹, —C(═O)OR⁹, —C(═O)NR¹⁰R¹¹, —OC(═O)R⁹,    —OC(═O)OR⁹, and —OC(═O)NR¹⁰R¹¹;-   Each R¹² and R¹³ is independently C₁₋₆ alkyl, C₁₋₆ alkoxy, C₃₋₈    cycloalkyl, aryl, heteroaryl, heterocyclyl, or R¹² and R¹³ are taken    together with the phosphorus atom to which they are attached to form    a 4- to 8-membered heterocyclyl optionally substituted with one or    more groups selected from the group consisting of halo, hydroxyl,    alkyl, alkenyl, alkynyl, haloalkyl, hydroxyalkyl, —CN, —NO₂,    —NR¹⁰R¹¹, —NR¹⁰C(═O)R⁹, —NR¹⁰C(═O)NR¹⁰R¹¹, —NR¹⁰C(═O)OR⁹, —OR⁹,    —C(═O)R⁹, —C(═O)OR⁹, —C(═O)NR¹⁰R¹¹, —OC(═O)R⁹, —OC(═O)OR⁹, and    —OC(═O)NR¹⁰R¹¹; Het is selected from the group consisting of:

-   Each of R^(a), R^(b) and R^(c) is independently —H, -D, halo, CF₃,    CF₂H, CH₂F, CN, OR⁹ or NR¹⁰R¹¹;-   R² is —H, -D, —CD₃, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl,    cycloalkyl, aryl, heteroaryl, heterocyclyl, halo, hydroxyl, —CD₂OH,    —CN, —NO₂, haloalkyl, trimethylsilylethoxymethyl, —C(O)R⁹, —C(O)OR⁹,    —C(O)NR¹⁰R¹¹, —OR⁹, —OC(O)R⁹, —OC(O)NR¹⁰R¹¹, —SR⁹, —S(O)R⁹,    —S(O)₂R⁹, —S(O)(═NH)R₁₀, —S(O)₂NR¹⁰R¹¹, —NR¹⁰R¹¹, —N(R⁶)NR¹⁰R¹¹,    —N(R⁶)OR⁹, —N(R⁶)C(O)R⁹, —N(R⁶)C(O)R⁹, —N(R⁶)C(O)OR⁹,    —N(R⁶)C(O)NR¹⁰R¹¹, —N(R⁶)S(O)₂R⁹, —N(R⁶)S(O)₂NR¹⁰R¹¹, or —P(O)R¹²R¹³    wherein the C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, cycloalkyl,    aryl, heteroaryl, or heterocyclyl is optionally substituted with one    or more groups selected from the group consisting of halo, hydroxyl,    alkyl, alkenyl, alkynyl, haloalkyl, hydroxyalkyl, —CN, —NO₂,    —NR¹⁰R¹¹, —NR¹⁰C(═O)R⁹, —NR¹⁰C(═O)NR¹⁰R¹¹, —NR¹⁰C(═O)OR⁹, —OR⁹,    —C(═O)R⁹, —C(═O)OR⁹, —C(═O)NR¹⁰R¹¹, —OC(═O)R⁹, —OC(═O)OR⁹, and    —OC(═O)NR¹⁰R¹¹;-   R³ is —H, -D, —CD₃, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl,    cycloalkyl, aryl, heteroaryl, heterocyclyl, halo, cyano, hydroxy,    —CH₂OH, —CD₂OH, —OH, —CN, —NO₂, haloalkyl, —C(O)R⁹, —C(O)OR⁹,    —C(O)NR¹⁰R¹¹, —OR⁹, —OC(O)R⁹, —OC(O)NR¹⁰R¹¹, —SR⁹, —S(O)R⁹,    —S(O)₂R⁹, —S(O)(═NH)R₁₀, —S(O)₂NR¹⁰R¹¹, —NR¹⁰R¹¹, —N(R⁶)NR¹⁰R¹¹,    —N(R⁶)OR⁹, —N(R⁶)C(O)R⁹, —N(R⁶)C(O)OR⁹, —N(R⁶)C(O)NR¹⁰R¹¹,    —N(R⁶)S(O)₂R⁹, —N(R⁶)S(O)₂NR¹⁰R¹¹, or —P(O)R¹²R¹³;-   M is a bond, —O—, —S—, or —NR⁶—;-   R⁶ is —H or C₁₋₆ alkyl;-   R⁴ is —H, -D, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, cycloalkyl,    aryl, heteroaryl, heterocyclyl, halo, cyano, hydroxy, —C(O)R⁹,    —C(O)OR⁹, —C(O)NR¹⁰R¹¹, —S(O)₂R⁹, —S(O)(═NH)R¹⁰, —S(O)₂NR¹⁰R¹¹, or    —P(O)R¹²R¹³, wherein C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl,    cycloalkyl, aryl, heteroaryl, or heterocyclyl is optionally    substituted with one or more groups selected from the group    consisting of halo, hydroxyl, alkyl, alkenyl, alkynyl, haloalkyl,    hydroxyalkyl, —CN, —CD₃, —NO₂, —NR¹⁰R¹¹, —NR¹⁰C(═O)R⁹,    —NR¹⁰C(═O)NR¹⁰R¹¹, —NR¹⁰C(═O)OR⁹, —NR¹⁰S(O)₂R⁹, —OR⁹, —C(═O)R⁹,    —C(═O)OR⁹, —C(═O)NR¹⁰R¹¹, —OC(═O)R⁹, —OC(═O)OR⁹, and —OC(═O)NR¹⁰R¹¹;    and-   R⁵ is —H, -D, —CD₃, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl,    cycloalkyl, halo, hydroxyl, —CH₂OH, —CD₂OH, —CN or haloalkyl.

In various embodiments, L is a bond, and R¹ is cycloalkyl which isoptionally substituted with one or more groups selected from the groupconsisting of C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, cycloalkyl, halo,cyano, hydroxy, —C(O)R⁹, —C(O)OR⁹, —C(O)NR¹⁰R¹¹, —OR⁹, —OC(O)R⁹,—OC(O)NR¹⁰R¹¹, —NR¹⁰R¹¹, —N(R⁶)NR¹⁰R¹¹, —N(R⁶)OR⁹, —N(R⁶)C(O)R⁹,—N(R⁶)C(O)OR⁹, and —N(R⁶)C(O)NR¹⁰R¹¹. In various embodiments, each of R²and R³ is independently —H, halo, alkylthio, haloalkyl, or alkyl. Invarious embodiments, M is a bond, —O—, or —NR⁶—; and R⁴ is —H, -D, C₁₋₆alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, cycloalkyl, aryl, heteroaryl,heterocyclyl, halo, cyano, hydroxy, —C(O)R⁹, —C(O)NR¹⁰R¹¹, —S(O)₂R⁹,—S(O)(═NH)R¹⁰, or —S(O)₂NR¹⁰R¹¹, wherein the C₁₋₆ alkyl, C₂₋₆ alkenyl,C₂₋₆ alkynyl, cycloalkyl, aryl, heteroaryl, or heterocyclyl isoptionally substituted with one or more groups selected from the groupconsisting of halo, hydroxy, alkyl, alkenyl, alkynyl, haloalkyl,hydroxyalkyl, —CN, —CD₃, —NR¹⁰R¹¹, —NR¹⁰S(O)₂R⁹, and —NR¹⁰C(═O)R⁹.

In another embodiment, there is provided a compound represented byFormula (II):

wherein R¹, R², R³, R⁴, R⁵, R^(a), R^(b), M, and L are as defined abovefor Formula (I).

In various embodiments, L is a bond, R¹ is cyclopropyl which isoptionally substituted with one or more groups selected from the groupconsisting of halo, C₁₋₃ alkylthio, C₁₋₃ alkyl, C₁₋₃ hydroxyalkyl andC₁₋₃ haloalkyl; R² is —H, alkyl, halo, haloalkyl, or alkylthio; R³ is—H, alkyl, or halo; M is a bond, —O—, —S— or —NR⁶—; R⁴ is —H, halo,alkyl, hydroxyalkyl, haloalkyl, haloalkenyl, cycloalkyl, cyanoalkyl,dimethylamino, dimethylaminoethyl, dimethylaminocarbonyl,methylaminooxoethyl, aminocarbonylalkyl, acetamindoethyl,propionamidoethyl, formamidoethyl, aminoalkyl,methylaminocarbonylmethyl, alkoxyalkyl, azetidinyl, or azetidinylmethyl;and R⁵ is —H, alkyl, or halo.

Non-limiting exemplary compounds of Formula (II) include the compound ofExamples 1-145 of Table 1. In particular embodiments, the compound isselected from the group consisting of: the compounds of Examples 58, 80,82, 85, 87, 92, 94, 97, 98, 110, 111, 118, 123, 125, 129, and 134.

In another embodiment, there is provided a compound represented byFormula (III):

wherein R¹, R², R³, R⁴, R⁵, R^(a), R^(b), M, and L are as defined abovefor Formula (I).

In some embodiments, L is a bond, R¹ is cyclopropyl which is optionallysubstituted with one or more groups selected from the group consistingof halo, C₁₋₃ alkyl, C₁₋₃ hydroxyalkyl and C₁₋₃ haloalkyl; R² is —H,alkyl, halo, haloalkyl, or alkylthio; R³ is —H, alkyl, or halo; M is abond, —O—, —S— or —NR⁶—; R⁴ is —H, halo, alkyl, hydroxyalkyl,dimethylamino, dimethylaminoethyl, dimethylaminocarbonyl,methylaminooxoethyl, aminocarbonylalkyl, acetamindoethyl, oralkoxyalkyl; and R⁵ is —H, alkyl, or halo.

Non-limiting exemplary compounds of Formula (III) include the compoundof Examples 146-218 of Table 1. In particular embodiments, the compoundis selected from the group consisting of the compounds of Examples 149,152, 156, 159, 161-163, 167, 169, 170, 172-175, 178, 184, 193, 194, 196,199, and 218.

In another embodiment, there is provided a compound represented byFormula (IV):

wherein R¹, R², R³, R⁴, R⁵, R^(a), R^(b), M, and L are as defined abovefor Formula (I).

In some embodiments, L is a bond, R¹ is cyclopropyl which is optionallysubstituted with one or more groups selected from the group consistingof halo, C₁₋₃ alkyl, C₁₋₃ hydroxyalkyl and C₁₋₃ haloalkyl; R² is —H,alkyl, halo, haloalkyl, or alkylthio; R³ is —H, alkyl, or halo; M is abond, —O—, —S— or —NR⁶—; R⁴ is —H, halo, alkyl, hydroxyalkyl, haloalkyl,haloalkenyl, cycloalkyl, cyanoalkyl, dimethylamino, dimethylaminoethyl,dimethylaminocarbonyl, methylaminooxoethyl, aminocarbonylalkyl,acetamindoethyl, propionamidoethyl, formamidoethyl, cycloalkylalkyl,cycloalkyl(hydroxy)alkyl, hydroxycycloalkyl, methoxycycloalkyl,cycloalkyl(methoxy)methyl, alkoxyalkyl, alkenyl, methylsulfonamidoethyl,imidazolylethyl, dioxanyl, cyclobutanylcarbonylaminoethyl,difluoroacetamidoethyl, trifluoroacetamidoethyl, methylthiomethyl,methylthioethyl, azetidinyl, azetidinylmethyl,cyclopropylcarbonylamino(cyano)methyl, cyano(difluoroacetamido)methyl,propanyl-1,1,1,3,3,3-d6)amino, tetrahydrofuranyl, methylimidazolylethyl,furanyl, pyrrolyl, methylpyrrolyl, isoxazolyl, tetrazolylalkyl,methylpyrazolyl, or methylpyrazolylmethyl; and R⁵ is —H, alkyl, or halo.

Non-limiting exemplary compounds of Formula (IV) include the compound ofExamples 219 and 220 of Table 1.

In another embodiment, there is provided a compound represented byFormula (V):

wherein R¹, R², R³, R⁴, R⁵, R^(a), R^(b), M, and L are as defined abovefor Formula (I).

In some embodiments, L is a bond, and R¹ is cycloalkyl which isoptionally substituted with one or more groups selected from the groupconsisting of C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, cycloalkyl, halo,cyano, hydroxy, —C(O)R⁹, —C(O)OR⁹, —C(O)NR¹⁰R¹¹, —OR⁹, —OC(O)R⁹,—OC(O)NR¹⁰R¹¹, —NR¹⁰R¹¹, —N(R⁶)NR¹⁰R¹¹, —N(R⁶)OR⁹, —N(R⁶)C(O)R⁹,—N(R⁶)C(O)OR⁹, and —N(R⁶)C(O)NR¹⁰R¹¹. In some other embodiments, R¹ iscycloalkyl which is optionally substituted with one or more groupsselected from the group consisting of halo, C₁₋₃ alkyl, C₁₋₃hydroxyalkyl and C₁₋₃ haloalkyl.

Non-limiting exemplary compounds of Formula (V) include the compound ofExamples 221-445 of Table 1.

In some embodiments, R¹ is cyclopropyl which is optionally substitutedwith one or more groups selected from the group consisting of halo,C₁-C₃ alkyl, C₁-C₃ hydroxyalkyl and C₁-C₃ haloalkyl; R² is —H, alkyl,alkylthio, haloalkyl, or halo; R³ is —H, alkyl, or halo; M is a bond,—O—, or —NR⁶—; R⁴ is —H, halo, alkyl, monoalkylamino, or dialkylamino;R⁵ is —H, alkyl, or halo. Non-limiting exemplary compounds include oneselected from the group consisting of:

-   (1S,2S)—N-(6-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;-   (1S,2S)—N-(6-(7-(dimethylamino)-6-fluoro-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;-   (1S,2S)—N-(6-(7-(dimethylamino)-6-fluoro-5-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;-   (1S,2S)—N-(6-(7-(dimethylamino)-6-fluoro-5-(trifluoromethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;-   (1S,2S)—N-(6-(5-chloro-6-fluoro-7-(isopropylamino)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;    and-   (1S,2S)—N-(6-(5-chloro-6-fluoro-7-isopropyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide.

In some embodiments, R¹ is cyclopropyl which is optionally substitutedwith one or more groups selected from the group consisting of halo, C₁₋₃alkyl, C₁₋₃ hydroxyalkyl and C₁₋₃ haloalkyl; R² is —H, alkyl, halo,haloalkyl, or alkylthio; R³ is —H, alkyl, or halo; M is a bond, —O—, —S—or —NR⁶—; R⁴ is —H, halo, alkyl, hydroxyalkyl, haloalkyl, haloalkenyl,cycloalkyl, monoalkylamino, or dialkylamino; and R⁵ is —H, alkyl, orhalo. Non-limiting exemplary compounds include one selected from thegroup consisting of: the compounds of Examples 258, 261, 265, 266, 269,272, 275, 280, 288, 291, 293, 296, 297, 300, 304, 306, 310, 318, 320,324, 327, 329, 330, 332, 334, 336, 341, 345, 349, 353, 356, 358, 359,361, 366, 371, 372, 374, 390, 391, 393, 404, 405, 408, 410, 414, 417,419, 422, 423, 425, 426, 428, 430, 433, 434, 436, 439, 441, and 445.

In some embodiments, R¹ is cyclopropyl which is optionally substitutedwith one or more groups selected from the group consisting of halo, C₁₋₃alkyl, C₁₋₃ hydroxyalkyl and C₁₋₃ haloalkyl; R² is —H, alkyl, halo,haloalkyl, or alkylthio; R³ is —H, alkyl, or halo; M is a bond, —O—, —S—or —NR⁶—; R⁴ is —H, halo, alkyl, alkylcarbonyl, dialkylaminocarbonyl,oxopyrrolidinyl, hydroxyalkyl, haloalkyl, haloalkenyl, cycloalkyl,pyridinyl, monoalkylamino, or dialkylamino; and R⁵ is —H, alkyl, orhalo. Non-limiting exemplary compounds include one selected from thegroup consisting of the compounds of Examples 258, 261, 265, 266, 268,269, 271-273 275, 280, 281, 288, 290, 291, 293, 296-298, 300, 304, 306,307, 310, 316, 318, 320, 324, 326, 327, 329, 330-334, 336, 339, 341,345, 346, 349, 353, 356, 358, 359, 361-363, 365-367, 370-374, 377-379,383, 388, 390, 391, 393, 398, 401, 404-406, 408-410, 414, 415, 417, 419,421-426, 428, 430, 433, 434, 436, 439, 441, and 445.

In another embodiment, there is provided a compound represented byFormula (VI):

wherein R¹, R², R³, R⁴, R⁵, R^(a), R^(b), M, and L are as defined abovefor Formula (I).

In some embodiments, L is a bond, R¹ is cyclopropyl which is optionallysubstituted with one or more groups selected from the group consistingof halo, C₁₋₃ alkyl, C₁₋₃ hydroxyalkyl and C₁₋₃ haloalkyl; R² is —H,alkyl, halo, haloalkyl, or alkylthio; R³ is —H, alkyl, or halo; M is abond, —O—, —S— or —NR⁶—; R⁴ is —H, halo, alkyl, hydroxyalkyl, haloalkyl,haloalkylamidoalkyl, haloalkylcarbonylaminoalkyl, alkylamidoalkyl,hydroxyhaloalkyl, haloalkenyl, cycloalkyl, cyano, cyanoalkyl,dimethylamino, dimethylaminoethyl, methylaminocarbonyl,dimethylaminocarbonyl, methylaminooxoethyl, aminocarbonylalkyl,acetamindoethyl, dialkylaminocycloalkyl, aminocycloalkyl,methylaminocycloalkyl, cycloalkylalkyl, cycloalkyl(hydroxy)alkyl,cycloalkylamidoalkyl, cycloalkylaminocarbonyl, hydroxycycloalkyl,methoxycycloalkyl, cycloalkyl(methoxy)methyl, alkoxycarbonyl,alkylcarbonyl, alkylamidoalkyl, alkoxyalkyl, alkenyl,methylsulfonamidoethyl, imidazolylethyl, dioxanyl, azetidinyl,azetidinylmethyl, tetrahydrofuranyl, furanyl, pyrimidinyl, pyridinyl,pyrrolyl, halopyrrolidinyl, pyrrolidinyl, methylpyrrolyl, isoxazolyl,tetrazolylalkyl, triazinyl, methylpyrazolyl, or methylpyrazolylmethyl;and R⁵ is —H, alkyl, or halo.

Non-limiting exemplary compounds of Formula (VI) include the compound ofExamples 446-666 of Table 1. In particular embodiments, the compound isselected from the group consisting of the compounds of Examples 464,466, 467, 476, 477, 480, 484, 485, 487, 488, 490-494, 496, 497, 502-505,509, 513, 514, 519-521, 523-525, 529-532, 534, 541, 543, 548, 550, 552,556-558, 561-565, 568-574, 577, 579, 581, 585, 586, 588, 592, 596-600,602, 607, 612, 615, 617-619, 621, 623, 625, 629, 634, 636-642, 644, 646,650-652, 655-657, and 659-665.

In an embodiment, there is provided a pharmaceutical compositioncomprising a pharmaceutically acceptable carrier or diluent and acompound of Formula (I) or a pharmaceutically acceptable salt thereof.

Medical Uses and Methods of Treatment Using the Compounds

The present disclosure provides a method of treating a subject with adisease or disorder associated with modulation of HPK1 comprising:administering to the subject in need thereof a therapeutically effectiveamount of the compound of Formula (I) or a pharmaceutically acceptablesalt thereof. In some embodiments, the disease or disorder associatedwith modulation of HPK1 is a cancer, metastasis, inflammation, or immunedisease including autoimmune disease.

In some other embodiments, the disease is cancer, metastasis,inflammation or auto-immune disease. In particular embodiments, thecancer is selected from the group consisting of carcinomas, melanomas,blastomas, sarcomas, lymphomas and leukemias, including withoutlimitation, bladder carcinoma, brain tumors, breast cancer, cervicalcancer, colorectal cancer, esophageal cancer, endometrial cancer,hepatocellular carcinoma, laryngeal cancer, lung cancer, osteosarcoma,ovarian cancer, pancreatic cancer, prostate cancer, renal carcinoma andthyroid cancer, acute lymphocytic leukemia, acute myeloid leukemia,ependymoma, Ewing's sarcoma, glioblastoma, medulloblastoma,neuroblastoma, osteosarcoma, rhabdomyosarcoma, rhabdoid cancer, andnephroblastoma (Wilm's tumor).

In some embodiments, the autoimmune disease is an inflammatory boweldisease, Addison's disease, alopecia areata, ankylosing spondylitis,antiphospholipid syndrome, hemolytic anemia, autoimmune hepatitis,Behcet's disease, Berger's disease, bullous pemphigoid, cardiomyopathy,celiac sprue, chronic fatigue immune dysfunction syndrome (CFIDS),chronic inflammatory demyelinating polyneuropathy, Churg-Strausssyndrome, cicatricial pemphigoid, cold agglutinin disease, type 1diabetes, discoid lupus, essential mixed cryoglobulinemia, Graves'disease, Guillain-Barre syndrome, Hashimoto's thyroiditis,hypothyroidism, autoimmune lymphoproliferative syndrome (ALPS),idiopathic pulmonary fibrosis, idiopathic thrombocytopenia purpura(ITP), juvenile arthritis, lichen planus, lupus erythematosus, Meniere'sdisease, mixed connective tissue disease, multiple sclerosis, myastheniagravis, pemphigus vulgaris, pernicious anemia, polychondritis,autoimmune polyglandular syndromes, polymyalgia rheumatica,polymyositis, dermatomyositis, primary agammaglobulinemia, primarybiliary cirrhosis, psoriasis, psoriatic arthritis, Raynaud's phenomenon,Reiter's syndrome, rheumatic fever, rheumatoid arthritis, sarcoidosis,scleroderma, Sjogren's syndrome, stiff-man syndrome, Takayasu arteritis,giant cell arteritis, ulcerative colitis, uveitis, vasculitis, orgranulomatosis with polyangiitis.

In another embodiment, there is provided the use of a compound ofFormula (I) or a pharmaceutically acceptable salt thereof for themanufacture of a medicament for inhibiting HPK1 activity in a subject inneed of inhibition of HPK1 activity. In some embodiments, the useincludes treatment of cancer.

Suitable subjects to be treated according to the present disclosureinclude mammalian subjects. Mammals according to the present disclosureinclude, but are not limited to, human, canine, feline, bovine, caprine,equine, ovine, porcine, rodents, lagomorphs, primates, and the like, andencompass mammals in utero. Subjects may be of either gender and at anystage of development. In one embodiment, the suitable subject to betreated according to the present disclosure is human.

The compounds of the present disclosure are generally administered in atherapeutically effective amount. The compounds of the presentdisclosure can be administered by any suitable route in the form of apharmaceutical composition adapted to such a route, and in a doseeffective for the treatment intended. An effective dosage is typicallyin the range of about 0.01 to about 1000 mg per kg body weight per day,preferably about 0.01 to about 500 mg/kg/day, in single or divideddoses. Depending on age, species and disease or condition being treated,dosage levels below the lower limit of this range may be suitable. Inother cases, still larger doses may be used without harmful sideeffects. Larger doses may also be divided into several smaller doses,for administration throughout the day. Methods for determining suitabledoses are well known in the art to which the present disclosurepertains. For example, Remington: The Science and Practice of Pharmacy,Mack Publishing Co., 20^(th) ed., 2000 can be used.

Pharmaceutical Compositions, Dosage Forms and Administration Routes

For the treatment of the diseases or conditions referred to above, thecompounds described herein or pharmaceutically acceptable salts thereofcan be administered as follows:

Oral Administration

The compounds of the present disclosure may be administered orally,including by swallowing, so that the compound enters thegastrointestinal tract, or absorbed into the blood stream directly fromthe mouth (e.g., buccal or sublingual administration). Suitablecompositions for oral administration include solid, liquid, gel orpowder formulations, and have a dosage form such as tablet, lozenge,capsule, granule or powder. Compositions for oral administration may beformulated as immediate or modified release, including delayed orsustained release, optionally with enteric coating. Liquid formulationscan include solutions, syrups and suspensions, which can be used in softor hard capsules. Such formulations may include a pharmaceuticallyacceptable carrier, for example, water, ethanol, polyethylene glycol,cellulose, or an oil. The formulation may also include one or moreemulsifying agents and/or suspending agents.

In a tablet dosage form the amount of drug present may be from about0.05% to about 95% by weight, more typically from about 2% to about 50%by weight of the dosage form. In addition, tablets may contain adisintegrant, comprising from about 0.5% to about 35% by weight, moretypically from about 2% to about 25% of the dosage form. Examples ofdisintegrants include, but are not limited to, lactose, starch, sodiumstarch glycolate, crospovidone, croscarmellose sodium, maltodextrin, ormixtures thereof.

Suitable lubricants, for use in a tablet, may be present in amounts fromabout 0.1% to about 5% by weight, and include, but are not limited to,talc, silicon dioxide, stearic acid, calcium, zinc or magnesiumstearate, sodium stearyl fumarate and the like.

Suitable binders, for use in a tablet, include, but are not limited to,gelatin, polyethylene glycol, sugars, gums, starch, polyvinylpyrrolidone, hydroxypropyl cellulose, hydroxypropylmethyl cellulose andthe like. Suitable diluents, for use in a tablet, include, but are notlimited to, mannitol, xylitol, lactose, dextrose, sucrose, sorbitol,microcrystalline cellulose and starch.

Suitable solubilizers, for use in a tablet, may be present in amountsfrom about 0.1% to about 3% by weight, and include, but are not limitedto, polysorbates, sodium lauryl sulfate, sodium dodecyl sulfate,propylene carbonate, diethyleneglycol monoethyl ether, dimethylisosorbide, polyethylene glycol (natural or hydrogenated) castor oil,HCOR™ (Nikkol), oleyl ester, Gelucire™, caprylic/caprylic acidmono/diglyceride, sorbitan fatty acid esters, and Solutol HS™.

Parenteral Administration

Compounds of the present disclosure may be administered directly intothe blood stream, muscle, or internal organs. Suitable means forparenteral administration include intravenous, intra-muscular,subcutaneous intraarterial, intraperitoneal, intrathecal, intracranial,and the like. Suitable devices for parenteral administration includeinjectors (including needle and needle-free injectors) and infusionmethods.

Compositions for parenteral administration may be formulated asimmediate or modified release, including delayed or sustained release.Most parenteral formulations are aqueous solutions containingexcipients, including salts, buffering agents and isotonic agents.Parenteral formulations may also be prepared in a dehydrated form (e.g.,by lyophilization) or as sterile non-aqueous solutions. Theseformulations can be used with a suitable vehicle, such as sterile water.Solubility-enhancing agents may also be used in preparation ofparenteral solutions.

Transdermal Administration

Compounds of the present disclosure may be administered topically to theskin or transdermally. Formulations for this topical administration caninclude lotions, solutions, creams, gels, hydrogels, ointments, foams,implants, patches and the like. Pharmaceutically acceptable carriers fortopical administration formulations can include water, alcohol, mineraloil, glycerin, polyethylene glycol and the like. Topical or transdermaladministration can also be performed by electroporation, iontophoresis,phonophoresis and the like. Compositions for topical administration maybe formulated as immediate or modified release, including delayed orsustained release.

Combination Therapy

A pharmaceutical composition according to the present disclosure maycontain one or more additional therapeutic agents, for example, toincrease the efficacy or decrease the side effects. In some embodiments,accordingly, a pharmaceutical composition further contains one or moreadditional therapeutic agents selected from active ingredients useful totreat or inhibit diseases mediated directly or indirectly by HPK1.Examples of such active ingredients are, without limitation, agents totreat cancer, metastasis, inflammation, or auto-immune pathogenesis. Insome embodiments, the compound of Formula (I) is administered withanti-PD-1 agent, anti-PD-L1 agent, or anti-CTLA4 agent.

References for Preparing Pharmaceutical Compositions

Methods for preparing pharmaceutical compositions for treating orpreventing a disease or condition are well known in the art to which thepresent disclosure pertains. For example, based on Handbook ofPharmaceutical Excipients (7^(th) ed.), Remington: The Science andPractice of Pharmacy (20^(th) ed.), Encyclopedia of PharmaceuticalTechnology (3^(rd) ed.), or Sustained and Controlled Release DrugDelivery Systems (1978), pharmaceutically acceptable excipients,carriers, additives and so on can be selected and then mixed with thecompounds of the present disclosure for making the pharmaceuticalcompositions.

The present disclosure provides a compound having variouspharmacological effects by inhibiting HPK1 activity, a pharmaceuticalcomposition having the compound as an effective agent, a medical use,particularly for treating a disease or disorder modulated by HPK1, ofthe compound, and a method of treatment or prevention comprisingadministering the compound to a subject in need of such treatment orprevention. The compounds of the present disclosure and pharmaceuticallyacceptable salts thereof have good safety and high selectivity for HPK1,and thus exhibit superior property as a drug.

Compound Preparation

The following Preparative Examples illustrate the preparation ofintermediate compounds that are useful for preparing compounds offormula (I). The novel intermediate compounds described herein, as wellas the synthetic processes useful for preparing the intermediatecompounds represent embodiments of the current invention.

Intermediate 1A.1-(tetrahydro-2H-pyran-2-yl)-5-(thiophen-2-yl)-1H-indazol-4-yltrifluoromethanesulfonate

Step 1) 3-bromo-4-chloro-5-fluoro-2-methylaniline

To a solution of 3-bromo-5-fluoro-2-methylaniline (50 g, 245 mmol, 1 eq)in AcOH (100 mL) was added N-chlorosuccinimide (36 g, 270 mmol, 1.1 eq).The mixture was stirred at 25° C. for 16 hr. The mixture wasconcentrated under vacuum and the residue was extracted withDichloromethane (200 mL*2). The combined organic layers were washed withsat. NaHCO₃ 200 mL, dried over Na₂SO₄, filtered and concentrated underreduced pressure to give a residue. The crude product (66 g, crude) wasobtained as a black oil.

Step 2) 4-bromo-5-chloro-6-fluoro-1H-indazole

To a solution of 3-bromo-4-chloro-5-fluoro-2-methylaniline (25.8 g, 108mmol, 1 eq) in AcOH (1.96 L, 0.05 M), H₂O (0.065 L, 1.5 M) was addedsodium nitrite (8.96 g, 130 mmol, 1.2 eq). The mixture was stirred at25° C. for 16 hr. The mixture was concentrated under vacuum and theresidue was extracted with Dichloromethane (1 L*2). The combined organiclayers were washed with sat. NaHCO₃ (1 L), dried over Na₂SO₄, filteredand concentrated under reduced pressure to give a residue. The crudeproduct (23.6 g, crude) was obtained as a brown solid.

Step 3)4-bromo-5-chloro-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

To a solution of 4-bromo-5-chloro-6-fluoro-1H-indazole (1.98 g, 7.97mmol, 1 eq) in THP (40 mL) was added 3,4-dihydro-2H-pyran (2.18 ml, 23.9mmol, 3 eq) and p-toluenesulfonic acid monohydrate (300 mg, 1.59 mmol,0.2 eq). The reaction mixture was stirred 70° C. for 14 hours. Thereaction mixture was extracted with Ethyl Acetate and dried over MgSO₄.The organic residue was purified by column chromatography (silical gel,Hex:Ethyl acetate=1:0 to 4:1).4-bromo-5-chloro-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (1.51g, 4.54 mmol, 57% yield) was obtained.

¹H NMR (400 MHz, DMSO-d₆) δ 8.16 (s, 1H), 8.00 (dd, J=9.3, 1.1 Hz, 1H),5.85 (dd, J=9.6, 2.5 Hz, 1H), 3.87 (d, J=12.6 Hz, 1H), 3.79-3.72 (m,1H), 2.38-2.30 (m, 1H), 2.04-1.94 (m, 2H), 1.77-1.55 (m, 3H).

Intermediate 1B.4-bromo-5-chloro-6-fluoro-7-iodo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole

Step 1) 4-bromo-5-chloro-6-fluoro-7-iodo-1H-indazole

To a solution of 4-bromo-5-chloro-6-fluoro-1H-indazole (2 g, 8.02 mmol)in sulfuric acid (1.7 mL) was added N-iodosuccinimide (2.7 g, 12.03mmol) portionwise. The mixture was stirred at 0° C. for 3 h. After thereaction completed, the mixture was poured into ice water and quenchedby solid NaOH and then extracted with Dichloromethane. The combinedorganic residue was concentrated in vacuo. (2.99 g, crude).

¹H NMR (400 MHz, DMSO-d₆) δ 13.91 (s, 1H), 8.27 (d, J=1.6 Hz, 1H).

Step 2)4-bromo-5-chloro-6-fluoro-7-iodo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole

To a solution of 4-bromo-5-chloro-6-fluoro-7-iodo-1H-indazole (2.99 g,7.97 mmol, 1 eq) in THF (40 mL) was added 3,4-dihydro-2H-pyran (2.18 ml,23.9 mmol, 3 eq) and p-toluenesulfonic acid monohydrate (300 mg, 1.59mmol, 0.2 eq). The reaction mixture was stirred 60° C. for 16 hours. Thereaction mixture was extracted with Ethyl Acetate and dried over MgSO₄.The organic residue was purified by column chromatography (silical gel,Hex:Ethyl acetate=1:0 to 4:1).4-bromo-5-chloro-6-fluoro-7-iodo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole(1.64 g, 7.97 mmol, 60.7% yield) was obtained.

¹H NMR (400 MHz, DMSO-d₆) δ 8.84 (s, 1H), 5.80 (dd, J=9.9, 2.7 Hz, 1H),5.66 (s, 1H), 4.02 (t, J=6.6 Hz, 1H), 3.85-3.70 (m, 1H), 2.33-2.21 (m,1H), 2.08-1.91 (m, 2H), 1.79-1.45 (m, 4H).

Intermediate 1C.4-bromo-5-chloro-6-fluoro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-7-amine

Step 1) 4-bromo-5-chloro-6-fluoro-7-nitro-1H-indazole

To a mixture of HNO₃ (12.63 g, 200.43 mmol, 9.02 mL, 5 eq) in H₂SO₄ (50mL) stirred at 0° C. was added 4-bromo-5-chloro-6-fluoro-1H-indazole (10g, 40.09 mmol, 1 eq) slowly. After the addition the mixture was stirredat 0° C. for 2 hr. TLC (Petroleum ether:Ethyl acetate=3:1) showed allthe reactant was consumed and a main new point showed up. Poured themixture into ice-water, extracted with ethyl acetate (50 mL*3), thecombined organic phase was dried over Na₂SO₄, filtered and the filtratewas concentrated to obtain 4-bromo-5-chloro-6-fluoro-7-nitro-1H-indazole(12 g, crude) as a yellow solid.

Step 2)4-bromo-5-chloro-6-fluoro-7-nitro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole

To a solution of 4-bromo-5-chloro-6-fluoro-7-nitro-1H-indazole (2.34 g,7.97 mmol, 1 eq) in THF (40 mL) was added 3,4-dihydro-2H-pyran (2.18 ml,23.9 mmol, 3 eq) and p-toluenesulfonic acid monohydrate (300 mg, 1.59mmol, 0.2 eq). The reaction mixture was stirred 60° C. for 14 hours. Thereaction mixture was extracted with Ethyl Acetate and dried over MgSO₄.The organic residue was purified by column chromatography (silical gel,Hex:Ethyl acetate=1:0 to 4:1).4-bromo-5-chloro-6-fluoro-7-nitro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole(1.65 g, 4.35 mmol, 54.7% yield) was obtained.

Step 3)4-bromo-5-chloro-6-fluoro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-7-amine

To a solution of4-bromo-5-chloro-6-fluoro-7-nitro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole(600 mg, 1.58 mmol, 1 eq) in EtOH (5 mL) and H₂O (5 mL) were added NH₄Cl(508.66 mg, 9.51 mmol, 6 eq) and Fe (531.04 mg, 9.51 mmol, 6 eq), thenthe reaction mixture was stirred at 80° C. for 1 hour. The reactionmixture was filtered, and the filtrate was diluted with ethyl acetate(20 mL), and the mixture was washed with water (20 mL*2), after then theorganic layer was dried over Na₂SO₄, filtered and concentrated underreduced pressure to give a residue. The residue was purified by prep-TLC(SiO₂, Petroleum ether/Ethyl acetate=1:1).4-bromo-5-chloro-6-fluoro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-7-amine(390 mg, 1.12 mmol, 70.59% yield) was obtained as a yellow oil.

¹H NMR (400 MHz, DMSO-d₆) δ 8.41 (s, 1H), 5.85 (br s, 2H), 5.71 (br d,J=8.0 Hz, 1H), 4.00 (br d, J=11.3 Hz, 1H), 3.77-3.59 (m, 1H), 2.29-2.17(m, 1H), 2.10-1.91 (m, 2H), 1.78-1.54 (m, 3H).

Intermediate 1D.4-bromo-5-chloro-6-fluoro-N,N-dimethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-7-amine

Step 1) 4-bromo-5-chloro-6-fluoro-7-nitro-1H-indazole

To a solution of Intermediate 1A (900 mg, 3.61 mmol, 1 eq) in H₂SO₄ (10mL) (98% purity) was added HNO₃ (419.69 mg, 4.33 mmol, 299.78 uL, 1.2eq) (65% purity) dropwise at −15° C., then the reaction mixture wasstirred at 0° C. for 2 hours. The reaction mixture was slowly pouredinto ice water (20 mL), then the mixture's pH was adjusted to pH=7 byusing saturated aqueous solution of NaOH, after then the mixture wasextracted with ethyl acetate (30 mL*2), the combined organic layers weredried over Na₂SO₄, filtered and concentrated under reduced pressure togive a residue. 4-bromo-5-chloro-6-fluoro-7-nitro-1H-indazole (900 mg,crude) was obtained as a yellow solid.

¹H NMR (400 MHz, DMSO-d₆) δ 14.36 (br s, 1H), 8.37 (br s, 1H).

Step 2)4-bromo-5-chloro-6-fluoro-7-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

To a solution of 4-bromo-5-chloro-6-fluoro-7-nitro-1H-indazole (900 mg,3.06 mmol, 1 eq) (crude) in DCM (10 mL) were added TsOH.H₂O (58.14 mg,305.64 umol, 0.1 eq) and DHP (771.27 mg, 9.17 mmol, 838.34 uL, 3 eq),then the reaction mixture was stirred at 20° C. for 2 hours. Thereaction mixture was diluted with dichloromethane (20 mL), and themixture was washed with saturated aqueous solution of NaHCO₃ (15 mL*2),the organic layer was dried over Na₂SO₄, filtered and concentrated underreduced pressure to give a residue. The residue was purified by columnchromatography (SiO2, Petroleum ether/Ethyl acetate=40/1 to 25:1,4-bromo-5-chloro-6-fluoro-7-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazolecame out at Petroleum ether/Ethyl acetate=40/1,4-bromo-5-chloro-6-fluoro-7-nitro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazolecame out at Petroleum ether/Ethyl acetate=25/1).4-bromo-5-chloro-6-fluoro-7-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole(200 mg, 528.29 umol, 17.28% yield) was obtained as a brown solid.4-bromo-5-chloro-6-fluoro-7-nitro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole(600 mg, 1.58 mmol, 51.85% yield) was obtained as a yellow solid.

4-bromo-5-chloro-6-fluoro-7-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

¹HNMR (400 MHz, DMSO-d₆) δ 8.43 (s, 1H), 5.50 (dd, J=2.8, 7.8 Hz, 1H),3.45-3.38 (m, 2H), 2.35-2.27 (m, 1H), 2.23-2.14 (m, 1H), 1.92 (td,J=4.6, 13.6 Hz, 1H), 1.68 (ddt, J=4.0, 10.1, 13.9 Hz, 1H), 1.59-1.36 (m,2H).

4-bromo-5-chloro-6-fluoro-7-nitro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole

¹H NMR (400 MHz, DMSO-d₆) δ 8.99 (s, 1H), 5.86 (dd, J=2.7, 9.7 Hz, 1H),4.08-3.96 (m, 1H), 3.81-3.68 (m, 1H), 2.28-2.14 (m, 1H), 2.14-2.02 (m,1H), 2.02-1.89 (m, 1H), 1.78-1.67 (m, 1H), 1.64-1.56 (m, 2H).

Step 3)4-bromo-5-chloro-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-7-amine

To a solution of4-bromo-5-chloro-6-fluoro-7-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole(200 mg, 528.29 umol, 1 eq) in EtOH (5 mL) and H₂O (5 mL) were addedNH₄Cl (169.55 mg, 3.17 mmol, 6 eq) and Fe (177.03 mg, 3.17 mmol, 6 eq),then the reaction mixture was stirred at 80° C. for 2 hours. Thereaction mixture was filtered, and the filtrate was concentrated toremove EtOH, then the mixture was diluted with ethyl acetate (20 mL),and the mixture was washed with water (20 mL*2), after then the organiclayer was dried over Na₂SO₄, filtered and concentrated under reducedpressure to give a residue.4-bromo-5-chloro-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-7-amine(140 mg, crude) was obtained as a yellow solid.

Step 4)4-bromo-5-chloro-6-fluoro-N,N-dimethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-7-amine

To a solution of4-bromo-5-chloro-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-7-amine(120 mg, 344.24 umol, 1 eq) in THF (5 mL) was added NaH (34.42 mg,860.59 umol, 60% purity, 2.5 eq) in portions at 0° C. under N₂, then themixture was stirred at 0° C. for 30 mins under N₂, after then Mel(293.16 mg, 2.06 mmol, 128.58 uL, 6 eq) was added dropwise, and thereaction mixture was stirred at 20° C. for 12 hours under N₂. Thereaction mixture was poured into saturated aqueous solution of NH₄Cl (20mL), then the mixture was extracted with ethyl acetate (20 mL*2), thecombined organic layers were dried over Na₂SO₄, filtered andconcentrated under reduced pressure to give a residue. The residue waspurified by prep-TLC (SiO₂, Petroleum ether/Ethyl acetate=5:1).Intermediate 1E (30 mg, 78.06 umol, 22.68% yield, 98% purity) wasobtained as a yellow oil.

Intermediate 1E.4-bromo-5-chloro-6-fluoro-N-isopropyl-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-7-amine

To a solution of Intermediate 1B (100 mg, 0.218 mmol, 1 eq) in2-methyl-2-butanol (1.09 mL) was added Xantphos Pd G3 (21 mg, 21.8 μmol,0.1 eq) and Cs₂CO₃ (142 mg, 0.436 mmol, 2.0 eq). The mixture wasdegassed and purged with N₂ for 3 times, and then propan-2-amine (0.19mL, 2.18 mmol, 10 eq) was added. The mixture was stirred at 90° C. for 3hr in sealed tube. The reaction mixture was diluted with H₂O (40 mL),and then the mixture was extracted with DCM (50 mL*3). The combinedorganic layers were dried over Na₂SO₄, filtered and the filtrate wasconcentrated in vacuum to give a residue. The residue was purified bysilica gel chromatography (product came out at Hexane/Ethylacetate=10/1) to afford Intermediate 1E (47 mg, 0.120 mmol, 55% yield)as beige color solid.

¹H NMR (400 MHz, DMSO-d₆) δ 8.43 (s, 1H), 5.74 (dd, J=9.6, 2.5 Hz, 1H),5.29 (dd, J=9.9, 3.3 Hz, 1H), 4.63-4.57 (m, 1H), 3.99 (d, J=11.0 Hz,1H), 3.74-3.68 (m, 1H), 2.23-2.17 (m, 1H), 2.05-1.95 (m, 2H), 1.74-1.57(m, 3H), 1.23-1.18 (m, 6H).

Intermediate 1F.4-bromo-5-chloro-6-fluoro-N-isopropyl-N-methyl-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-7-amine

To a solution of Intermediate 1E (600 mg, 1.54 mmol, 1.0 eq) in Methanol(7.7 mL) was added formaldehyde (0.572 mL, 7.68 mmol, 5.0 eq) and aceticacid (88 μL, 1.54 mmol, 1.0 eq). The mixture was stirred at roomtemperature for 10 min. Sodium cyanoborohydride (290 mg, 4.61 mmol, 3.0eq) was added and then the mixture was stirred room temperature for 16hr. The reaction mixture was quenched by H₂O and extracted with Ethylacetate (150 mL*3). The combined organic layers were dried over Na₂SO₄,filtered and the filtrate was concentrated in vacuum to give a residue.The residue was purified by silica gel chromatography (product came outat Hexane/Ethyl acetate=100/4) to afford Intermediate 1F (292 mg, 0.722mmol, 47% yield) as brown color oil.

¹H NMR (400 MHz, DMSO-d₆) δ 8.51 (s, 1H), 5.75 (dd, J=9.3, 2.7 Hz, 1H),4.14-4.05 (m, 1H), 4.00-3.93 (m, 1H), 3.78-3.67 (m, 1H), 2.92 (d, J=4.4Hz, 3H), 2.23-2.20 (m, 1H), 2.05-1.95 (m, 2H), 1.75-1.60 (m, 3H), 1.17(d, J=6.6 Hz, 6H).

Intermediate 1G.4-bromo-5-chloro-N-ethyl-6-fluoro-N-methyl-1H-indazol-7-amine

Step 1) 4-bromo-5-chloro-6-fluoro-1H-indazol-7-amine

To a solution of 4-bromo-5-chloro-6-fluoro-7-nitro-1H-indazole (12 g,40.75 mmol, 1 eq) in EtOH (100 mL) and H₂O (40 mL) was added Fe (6.83 g,122.26 mmol, 3 eq) and NH₄Cl (6.54 g, 122.26 mmol, 3 eq). The reactionmixture was heated to 80° C. and reacted for 2 hr. The reaction mixturewas filtered through a celite cake, the filtrate was concentrated togive the crude product. The residue was purified by columnchromatography (SiO₂, Petroleum ether/Ethyl acetate=20/1 to 3/1).4-bromo-5-chloro-6-fluoro-1H-indazol-7-amine (5 g, 18.90 mmol, 46.39%yield) was obtained as a yellow solid.

Step 2) N-(4-bromo-5-chloro-6-fluoro-1H-indazol-7-yl)acetamide

To a solution 4-bromo-5-chloro-6-fluoro-1H-indazol-7-amine (3 g, 11.34mmol, 1 eq) in AcOH (30 mL) was added Ac₂O (1.39 g, 13.61 mmol, 1.27 mL,1.2 eq), the reaction mixture was heated to 80° C. and reacted for 3 hr.The solvent was removed under vacuum. The residue was purified by columnchromatography (SiO₂, Petroleum ether/Ethyl acetate=50/1 to 4/1) toobtain N-(4-bromo-5-chloro-6-fluoro-1H-indazol-7-yl)acetamide (3 g, 9.79mmol, 86.29% yield) as a yellow solid.

Step 3) 4-bromo-5-chloro-N-ethyl-6-fluoro-1H-indazol-7-amine

To a solution of LAH (520.00 mg, 13.70 mmol, 1.5 eq) in THF (50 mL) wasadded a solution ofN-(4-bromo-5-chloro-6-fluoro-1H-indazol-7-yl)acetamide (2.8 g, 9.13mmol, 1 eq) in THF (100 mL) drop-wise under N₂ at 0° C., after theaddition, the reaction mixture was allowed to warm to 25° C., andreacted for 16 hr. The mixture was poured into water (500 mL), extractedwith ethyl acetate (100 mL*2), the combined organic phase was dried overNa₂SO₄, filtered and the filtrate was concentrated to give the crude.The residue was purified by column chromatography (SiO₂, Petroleumether/Ethyl acetate=50/1 to 2/1) to obtain4-bromo-5-chloro-N-ethyl-6-fluoro-1H-indazol-7-amine (1 g, 3.42 mmol,37.42% yield) as a yellow solid.

Step 4) 4-bromo-5-chloro-N-ethyl-6-fluoro-N-methyl-1H-indazol-7-amine

To a solution of 4-bromo-5-chloro-N-ethyl-6-fluoro-1H-indazol-7-amine(1.4 g, 4.79 mmol, 1 eq) and HCHO (718.48 mg, 23.93 mmol, 659.16 uL, 5eq) in MeOH (50 mL) was added NaBH3CN (902.21 mg, 14.36 mmol, 3 eq) andAcOH (287.38 mg, 4.79 mmol, 273.70 uL, 1 eq). The reaction mixture wasstirred at 25° C. for 16 hr. The solvent was removed under vacuum. Theresidue was purified by column chromatography (SiO₂, Petroleumether/Ethyl acetate=50/1 to 5/1) to obtain4-bromo-5-chloro-N-ethyl-6-fluoro-N-methyl-1H-indazol-7-amine (1.4 g,4.57 mmol, 95.42% yield) as a white solid.

Intermediate 1H.4-bromo-5-chloro-6-fluoro-7-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

To a solution of4-bromo-5-chloro-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (0.5g, 1.50 mmol, 1 eq) in THF (10 mL) was added dropwise LDA (2 M, 1.87 mL,2.5 eq) at −78° C. After addition, the mixture was stirred at thistemperature for 2.5 hr, and then Mel (319.12 mg, 2.25 mmol, 139.97 uL,1.5 eq) was added dropwise at −78° C. The resulting mixture was stirredat 20° C. for 16 hr. The mixture was poured into saturated NH₄Cl andextracted with EA 20 mL. The organic layer was concentrated. The residuewas purified by column chromatography (SiO₂, Petroleum ether/Ethylacetate=20/1 to 10/1). We got the desired product4-bromo-5-chloro-6-fluoro-7-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole(0.38 g, 1.09 mmol, 72.93% yield) was obtained as white solid.

Intermediate 1I.4-bromo-6-fluoro-N,N-dimethyl-5-(methylthio)-1H-indazol-7-amine

Step 1) 4-bromo-6-fluoro-7-nitro-1H-indazole

To a solution of 4-bromo-6-fluoro-1H-indazole (10 g, 46.51 mmol, 1 eq)in H₂SO₄ (80 mL) (98% purity) was added KNO₃ (4.70 g, 46.51 mmol, 1 eq)at 0° C. in portions, then the mixture was stirred at 0° C. for 1 h. Thereaction mixture was then poured into ice water (200 mL), and themixture was extracted with ethyl acetate (100 mL*2), the combinedorganic layers were washed with saturated aqueous solution of NaHCO₃(100 mL*2) and brine (100 mL), dried over Na₂SO₄, filtered andconcentrated under reduced pressure to give a residue. The residue waspurified by silica gel chromatography (200-300 mesh silica gel,Petroleum ether/Ethyl acetate=15/1 to 1/1, product4-bromo-6-fluoro-7-nitro-1H-indazole came out at Petroleum ether/Ethylacetate=8/1) to afford 4-bromo-6-fluoro-7-nitro-1H-indazole (2.7 g,10.38 mmol, 22.32% yield) as yellow solid and crude product. The curedproduct was purified by MPLC (Petroleum ether/Ethyl acetate) to afford4-bromo-6-fluoro-7-nitro-1H-indazole (3.57 g, 13.73 mmol, 29.52% yield)as yellow solid.

Step 2) 4-bromo-6-fluoro-5-iodo-7-nitro-1H-indazole

To a solution of 4-bromo-6-fluoro-7-nitro-1H-indazole (2.7 g, 10.38mmol, 1 eq) in H₂SO₄ (30 mL) was added NIS (7.01 g, 31.15 mmol, 3 eq) at25° C. The reaction mixture was stirred at 50° C. for 16 h. The reactionmixture was quenched by ice water (50 mL). Then the mixture wasextracted with ethyl acetate (50 mL*3). The combined organic layers werewashed with Na₂SO₃ aqueous solution (20 mL*2), NaHCO₃ aqueous solution(20 mL*2) and brine (20 mL), dried over sodium sulfate, filtered and thefiltrate was concentrated in vacuum to give4-bromo-6-fluoro-5-iodo-7-nitro-1H-indazole (3.4 g, 8.81 mmol, 84.85%yield) as yellow solid.

¹H NMR (400 MHz, DMSO-d₆) δ 14.28 (br s, 1H), 8.30 (s, 1H).

Step 3) 4-bromo-6-fluoro-5-iodo-1H-indazol-7-amine

To a solution of 4-bromo-6-fluoro-5-iodo-7-nitro-1H-indazole (3.4 g,8.81 mmol, 1 eq) in EtOH (50 mL) and H₂O (25 mL) was added NH₄Cl (2.83g, 52.86 mmol, 6 eq), then Fe (2.95 g, 52.86 mmol, 6 eq) was added inportions at 60° C. The mixture was stirred at 80° C. for 1 h. Thereaction mixture was filtered through celite while it was still hot.Then the filtrate was concentrated in vacuum to remove EtOH. Theresulting aqueous phase was extracted with ethyl acetate (50 mL*2). Thecombined organic layers were washed with brine (50 mL), dried oversodium sulfate, filtered and the filtrate was concentrated in vacuum togive a residue. The residue was purified by silica gel chromatography(MPLC, Petroleum ether/Ethyl acetate=5/1 to 2/1, product came out atPetroleum ether/Ethyl acetate=2/1) to afford4-bromo-6-fluoro-5-iodo-1H-indazol-7-amine (2.2 g, 6.18 mmol, 70.16%yield) as gray solid.

¹H NMR (400 MHz, DMSO-d₆) δ 13.09 (br s, 1H), 7.86 (d, J=1.7 Hz, 1H),5.62 (s, 2H).

Step 4) 4-bromo-6-fluoro-5-iodo-N,N-dimethyl-1H-indazol-7-amine

To a solution of 4-bromo-6-fluoro-5-iodo-1H-indazol-7-amine (2.2 g, 6.18mmol, 1 eq) in MeOH (50 mL) was added AcOH (1.11 g, 18.54 mmol, 1.06 mL,3 eq), HCHO (5.02 g, 61.81 mmol, 4.60 mL, 10 eq), then NaBH₃CN (3.88 g,61.81 mmol, 10 eq) was added in portions under 40° C. Gas released andthe temperature rise. The suspension was stirred at 25° C. for 16 h. Thereaction mixture was poured into water (50 mL), then the mixture wasconcentrated to remove MeOH, after then the mixture was extracted withethyl acetate (50 mL*2), and the combined organic layers were washedwith brine (50 mL), dried over sodium sulfate, filtered and concentratedunder reduced pressure to give a residue. The residue was purified bysilica gel chromatography (200-300 mesh silica gel, Petroleumether/Ethyl acetate=15/1 to 8/1, product came out at Petroleumether/Ethyl acetate=8/1) to afford4-bromo-6-fluoro-5-iodo-N,N-dimethyl-1H-indazol-7-amine (2.05 g, 5.34mmol, 86.37% yield) as off-white solid.

Step 5) 4-bromo-6-fluoro-N,N-dimethyl-5-(methylthio)-1H-indazol-7-amine

To a 100 mL bottle equipped with a magnetic stir bar was added4-bromo-6-fluoro-5-iodo-N,N-dimethyl-1H-indazol-7-amine (1.2 g, 3.13mmol, 1 eq), NaSMe (328.56 mg, 4.69 mmol, 1.5 eq), Xantphos (361.65 mg,625.02 umol, 0.2 eq), K₂CO₃ (1.30 g, 9.38 mmol, 3 eq), dioxane (20 mL)and Pd₂(dba)₃ (286.17 mg, 312.51 umol, 0.1 eq) sequentially. The bottlewas evacuated and backfilled with nitrogen. Then the mixture was stirredat 90° C. for 16 h under nitrogen atmosphere. The residue was purifiedby silica gel chromatography (200-300 mesh silica gel, Petroleumether/Ethyl acetate=20/1 to 8/1, product came out at Petroleumether/Ethyl acetate=10/1) to afford4-bromo-6-fluoro-N,N-dimethyl-5-(methylthio)-1H-indazol-7-amine (540 mg,1.78 mmol, 56.81% yield) as orange solid.

¹H NMR (400 MHz, DMSO-d₆) δ 13.59 (br s, 1H), 8.00 (d, J=1.6 Hz, 1H),2.91 (d, J=2.4 Hz, 6H), 2.39 (s, 3H).

Intermediate 1J.4-bromo-6-fluoro-N,N-dimethyl-5-(trifluoromethyl)-1H-indazol-7-amine

To a solution of 4-bromo-6-fluoro-5-iodo-N,N-dimethyl-1H-indazol-7-amine(1.0 g, 2.61 mmol, 1 eq) and methyl2,2-difluoro-2-(fluorosulfonyl)acetate (1.00 g, 5.22 mmol, 664.45 uL, 2eq) in DMF (10 mL) was added CuI (994.63 mg, 5.22 mmol, 2 eq). Themixture was stirred at 100° C. for 6 hr under N₂ atmosphere. Thereaction mixture was filtered and the filtrate was diluted with water 50mL and extracted with Ethyl acetate (50 mL*2). The combined organiclayers were washed with brine (50 mL*3), dried over anhydrous Na₂SO₄,filtered and the filtrate was concentrated under reduced pressure togive a residue. The residue was purified by silical gel columnchromatography (Petroleum ether:Ethyl acetate=1:0 to 10:1).4-bromo-6-fluoro-N,N-dimethyl-5-(trifluoromethyl)-1H-indazol-7-amine(502 mg, 1.54 mmol, 58.91% yield) was obtained as a yellow solid.

Intermediate 1K. 4-bromo-5-ethyl-6-fluoro-1H-indazole

Step 1) 4-bromo-5-ethyl-6-fluoro-2-trityl-2H-indazole

To a solution of diisopropylamine (132.75 mg, 1.31 mmol, 185.41 uL, 1.2eq) in THF (5 mL) was added slowly n-BuLi (2.5 M, 481.04 uL, 1.1 eq) at−78° C. for 0.5 hr under N₂ atmosphere. Then a solution of4-bromo-6-fluoro-2-trityl-2H-indazole (500 mg, 1.09 mmol, 1 eq) in THF(2 mL) was added dropwise to the solution. After the mixture was stirredat −78° C. for 0.5 hr, a solution of EtI (204.62 mg, 1.31 mmol, 104.93uL, 1.2 eq) in THF (2 mL) was added to the mixture and the solution werewarmed to 15° C. and stirred for 2 hr under N₂ atmosphere. The reactionmixture was quenched by addition with saturated NH₄Cl aqueous 3 mL at15° C., was diluted with water 20 mL and extracted with Ethyl acetate(30 mL*2). The combined organic layers were washed with brine (30 mL*2),dried over Na₂SO₄, filtered and the filtrate was concentrated underreduced pressure to give a residue.4-bromo-5-ethyl-6-fluoro-2-trityl-2H-indazole (500 mg, crude) wasobtained as a yellow solid.

Step 2) 4-bromo-5-ethyl-6-fluoro-1H-indazole

To a solution of 4-bromo-5-ethyl-6-fluoro-2-trityl-2H-indazole (500 mg,1.03 mmol, 1 eq) in DCM (6 mL) was added TFA (3.08 g, 27.01 mmol, 2.00mL, 26.22 eq). The mixture was stirred at 15° C. for 4 hr. The reactionmixture pH was adjusted to 7 with saturated NaHCO₃ aqueous, and themixture was extracted with Dichloromethane (30 mL*2). The combinedorganic layers were washed with brine (30 mL*2), dried over Na₂SO₄,filtered and the filtrate was concentrated under reduced pressure togive a residue. The residue was purified by prep-HPLC (column:Phenomenex luna C18 150*40 mm*15 um; mobile phase: [water (0.1%TFA)-ACN]; B %: 40%-70%, 10 min). The fraction was concentrated underreduced pressure to remove ACN, the aqueous pH was adjusted to 7 withsaturated NaHCO₃ aqueous. The aqueous was extracted with Ethyl acetate(10 mL*2). The combined organic layers were washed with brine (10 mL*2),dried over Na₂SO₄, filtered and the filtrate was concentrated underreduced pressure to give a product. 4-bromo-5-ethyl-6-fluoro-1H-indazole(70 mg, 287.98 umol, 27.96% yield) was obtained as a yellow solid.

¹H NMR (400 MHz, DMSO-d₆) δ 13.39 (br s, 1H), 8.01-7.98 (m, 1H), 7.41(d, J=9.9 Hz, 1H), 2.83 (dq, J=2.4, 7.5 Hz, 2H), 1.14 (t, J=7.5 Hz, 3H).

Intermediate 1L.4-bromo-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine

Step 1) 6-fluoro-5-nitro-1H-indazole

To a solution of 6-fluoro-1H-indazole (4.4 g, 32.32 mmol, 1 eq) in H₂SO₄(30 mL) was added HNO₃ (2.44 g, 38.79 mmol, 1.75 mL, 1.2 eq) dropwise at−15° C., the reaction mixture was stirred at 0° C. for 2 hours. Thereaction mixture was slowly poured into ice water (100 mL), then themixture was extracted with ethyl acetate (100 mL*2), the combinedorganic layers were dried over Na₂SO₄, filtered and concentrated underreduced pressure to give 6-fluoro-5-nitro-1H-indazole (5.4 g, crude) wasobtained as a yellow solid.

Step 2) 6-fluoro-5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

To a mixture of 6-fluoro-5-nitro-1H-indazole (4.9 g, 27.05 mmol, 1 eq)(crude) in DCM (50 mL) were added DHP (6.83 g, 81.16 mmol, 7.42 mL, 3eq) and TsOH.H₂O (514.60 mg, 2.71 mmol, 0.1 eq), and the reactionmixture was stirred at 15° C. for 1 hour. The reaction mixture waspoured into saturated solution of NaHCO₃ (100 mL), then the mixture wasextracted with dichloromethane (50 mL*2), the combined organic layerswere dried over Na₂SO₄, filtered and concentrated under reduced pressureto give a residue. The residue was purified by column chromatography(SiO₂, Petroleum ether/Ethyl acetate=20/1 to15:16-fluoro-5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (3 g,11.31 mmol, 41.81% yield) was obtained as a yellow solid.

¹H NMR (400 MHz, DMSO-d₆) δ 8.78 (d, J=7.3 Hz, 1H), 8.41 (s, 1H), 7.97(d, J=12.1 Hz, 1H), 5.90 (dd, J=2.1, 9.7 Hz, 1H), 3.94-3.85 (m, 1H),3.82-3.72 (m, 1H), 2.43-2.28 (m, 1H), 2.10-1.93 (m, 2H), 1.82-1.34 (m,3H).

Step 3) 6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine

To a solution of6-fluoro-5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (2.9 g, 10.93mmol, 1 eq) in MeOH (30 mL) was added wet Pd/C (300 mg, 10% purity)under N₂ atmosphere. The suspension was degassed and purged with H₂ for3 times. The mixture was stirred under H₂ (15 Psi) at 15° C. for 4hours. The reaction mixture was filtered, and the filtrate wasconcentrated under reduced pressure to give a residue. The residue waspurified by column chromatography (SiO₂, Petroleum ether/Ethylacetate=15/1 to 8:1).6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine (1.5 g, 5.87mmol, 53.65% yield, 92% purity) was obtained as a brick-red solid.

¹H NMR (400 MHz, DMSO-d₆) δ 7.82 (s, 1H), 7.43 (d, J=11.6 Hz, 1H), 6.98(d, J=8.6 Hz, 1H), 5.66 (dd, J=2.3, 9.7 Hz, 1H), 4.91 (s, 2H), 3.85 (brd, J=12.1 Hz, 1H), 3.77-3.62 (m, 1H), 2.42-2.27 (m, 1H), 2.07-1.96 (m,1H), 1.95-1.86 (m, 1H), 1.76-1.63 (m, 1H), 1.59-1.51 (m, 2H); LCMS(electrospray) m/z 236.1 (M+H)+.

Step 4) 4-bromo-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine

To a solution of6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine (1.45 g, 5.67mmol, 1 eq) in MeCN (10 mL) was added NBS (1.21 g, 6.80 mmol, 1.2 eq) inportions at 0° C. The mixture was stirred at 0° C. for 2 hours. Thereaction mixture was concentrated to give a residue. Then the residuewas dissolved in ethyl acetate (30 mL), and the mixture was washed withbrine (15 mL*2), the organic layer was dried over Na₂SO₄, filtered andconcentrated under reduced pressure to give a residue. The residue waspurified by column chromatography (SiO₂, Petroleum ether/Ethylacetate=20/1).4-bromo-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine (1.3 g,4.14 mmol, 72.98% yield) was obtained as a brown solid.

¹H NMR (400 MHz, DMSO-d₆) δ 7.80 (s, 1H), 7.60 (d, J=10.6 Hz, 1H), 5.71(dd, J=2.5, 9.6 Hz, 1H), 5.15 (s, 2H), 3.88-3.82 (m, 1H), 3.76-3.68 (m,1H), 2.36-2.27 (m, 1H), 2.02 (br dd, J=4.6, 8.5 Hz, 1H), 1.96-1.90 (m,1H), 1.76-1.65 (m, 1H), 1.60-1.52 (m, 2H).

Intermediate 1M.3-(4-bromo-5-chloro-6-fluoro-1H-indazol-7-yl)cyclopentan-1-ol

Step 1)4-bromo-5-chloro-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-7-carbaldehyde

To a mixture of Intermediate 1A (3 g, 8.99 mmol, 1 eq) in THF (60 mL)was added LDA (2 M, 17.99 mL, 4 eq) dropwise at −78° C. under N₂. Themixture was stirred at −78° C. for 1 h. After then, HCO₂Et (3.17 g,35.97 mmol, 3.52 mL, 4 eq) in THF (8 mL) was added dropwise at −78° C.,then the mixture was stirred at −78° C. for 2 h. The reaction mixturewas quenched by addition of saturated NH₄Cl solution (20 mL) at −78° C.,and then extracted with EA (30 mL*3). The combined organic layers werewashed with brine (30 mL*2), dried over Na₂SO₄, filtered andconcentrated under reduced pressure to give a residue. The residue waspurified by column chromatography (SiO₂, Petroleum ether/Ethylacetate=30/1 to 20/1).4-bromo-5-chloro-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-7-carbaldehyde(2.78 g, 7.69 mmol, 85.49% yield) was obtained as an off-white solid.

¹H NMR (400 MHz, DMSO-d₆) δ 10.40 (s, 1H), 8.35 (s, 1H), 6.09 (dd,J=2.6, 8.9 Hz, 1H), 3.71-3.63 (m, 1H), 3.63-3.52 (m, 1H), 2.42-2.30 (m,1H), 2.21-2.10 (m, 1H), 2.07-1.95 (m, 1H), 1.77-1.63 (m, 2H), 1.60-1.40(m, 2H); LCMS (electrospray) m/z 278.9 (M+H)+.

Step 2)1-(4-bromo-5-chloro-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-7-yl)but-3-en-1-ol

To a mixture of4-bromo-5-chloro-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-7-carbaldehyde(2.2 g, 6.08 mmol, 1 eq) in THF (60 mL) was added allyl magnesiumbromide (1 M, 9.13 mL, 1.5 eq) dropwise at 0° C. under N₂. The mixturewas stirred at 0° C. for 2 h. The reaction mixture was quenched byaddition of saturated NH₄Cl solution (20 mL) at 0° C., and thenextracted with EA (30 mL*3). The combined organic layers were washedwith brine (30 mL*2), dried over anhydrous Na₂SO₄, filtered andconcentrated under reduced pressure to give a residue. The residue waspurified by column chromatography (SiO₂, Petroleum ether/Ethylacetate=10/1 to 5/1).1-(4-bromo-5-chloro-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-7-yl)but-3-en-1-ol(2 g, 4.95 mmol, 81.43% yield) was obtained as a colorless oil.

¹H NMR (400 MHz, DMSO-d₆) δ 8.25-8.21 (m, 1H), 8.20-8.18 (m, 1H), 6.61(br d, J=9.0 Hz, 1H), 6.23 (d, J=4.0 Hz, 1H), 6.18 (br d, J=8.3 Hz, 1H),5.95 (d, J=5.0 Hz, 1H), 5.90-5.75 (m, 2H), 5.36 (dt, J=4.3, 7.5 Hz, 1H),5.30 (td, J=5.9, 7.9 Hz, 1H), 5.10-4.97 (m, 4H), 3.97 (br d, J=11.5 Hz,1H), 3.89 (br d, J=11.3 Hz, 1H), 3.69-3.55 (m, 2H), 2.87-2.74 (m, 2H),2.70-2.55 (m, 4H), 2.06 (br d, J=10.8 Hz, 3H), 1.96-1.87 (m, 1H),0.90-0.78 (m, 1H); LCMS (electrospray) m/z 302.9 (M+H)+.

Step 3) 4-bromo-7-(3-bromocyclopentyl)-5-chloro-6-fluoro-1H-indazole

To a mixture of1-(4-bromo-5-chloro-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-7-yl)but-3-en-1-ol(2 g, 4.95 mmol, 1 eq) in DCM (20 mL) was added Br₂ (1.19 g, 7.43 mmol,383.11 uL, 1.5 eq) in DCM (2 mL) dropwise at −20° C. under N₂. Themixture was stirred at −10° C. for 3 h. The mixture was quenched byaddition of Na₂SO₃ solution (30 mL), and then diluted with DCM (30 mL).The organic layer was washed with Na₂SO₃ solution (30 mL*2), dried overanhydrous Na₂SO₄, filtered and concentrated to obtain a residue. Theresidue was dissolved in MeOH (15 mL), and then K₂CO₃ (2.05 g, 14.86mmol, 3 eq) was added and the resulting mixture was stirred at 20° C.for 16 h. The reaction was quenched by addition of water (20 mL), andextracted with EA (30 mL*3), dried by Na₂SO₄, filtered and concentratedto obtain a residue. The residue was purified by column chromatography(SiO₂, Petroleum ether/Ethyl acetate=10/1 to 3:1). The crude product waspurified by reversed-phase HPLC (0.1% FA condition).4-bromo-7-(3-bromocyclopentyl)-5-chloro-6-fluoro-1H-indazole (300 mg,752.91 umol, 15.20% yield) was obtained as a white solid.

¹H NMR (400 MHz, DMSO-d₆) δ 13.44-13.37 (m, 2H), 8.14-8.11 (m, 2H),5.71-5.67 (m, 1H), 5.44 (dt, J=1.2, 7.5 Hz, 1H), 4.97 (s, 1H), 4.83-4.76(m, 2H), 4.47 (dd, J=3.7, 10.1 Hz, 1H), 4.22 (dd, J=5.5, 10.1 Hz, 1H),4.15 (dd, J=2.3, 10.6 Hz, 1H), 3.20-3.13 (m, 1H), 2.69-2.64 (m, 1H),2.34-2.27 (m, 2H); LCMS (electrospray) m/z 398.8 (M+H)+.

Step 4) 3-(4-bromo-5-chloro-6-fluoro-1H-indazol-7-yl)cyclopentyl acetate

To a mixture of4-bromo-7-(3-bromocyclopentyl)-5-chloro-6-fluoro-1H-indazole (100 mg,250.97 umol, 1 eq) in DMSO (2 mL) was added KOAc (73.89 mg, 752.91 umol,3 eq) in one portion at 20° C. under N₂. The mixture was then heated to70° C. and stirred for 3 h. The reaction was quenched by addition ofwater (15 mL), and then extracted with EA (20 mL*3), the combinedorganic layers were washed with brine (20 mL*2), dried by Na₂SO₄,filtered and concentrated to give a residue.3-(4-bromo-5-chloro-6-fluoro-1H-indazol-7-yl)cyclopentyl acetate (100mg, crude, brown oil) was used directly in the next step without furtherpurification.

LCMS (electrospray) m/z 378.8 (M+H)+.

Step 5) 3-(4-bromo-5-chloro-6-fluoro-1H-indazol-7-yl)cyclopentan-1-ol

To a mixture of 3-(4-bromo-5-chloro-6-fluoro-1H-indazol-7-yl)cyclopentylacetate (80 mg, 211.87 umol, 1 eq) in MeOH (4 mL) and H₂O (0.8 mL) wasadded K₂CO₃ (442.15 mg, 3.20 mmol, 15.1 eq) in one portion at 20° C.under N₂. The mixture was stirred at 20° C. for 2 h. The reactionmixture was quenched by addition of water (15 mL) at 20° C., and thenextracted with ethyl acetate (20 mL*3). The combined organic layers werewashed with brine (20 mL*1), dried over Na₂SO₄, filtered andconcentrated under reduced pressure to give a residue. The residue waspurified by column chromatography (SiO₂, Petroleum ether/Ethylacetate=3/1 to 1/2).3-(4-bromo-5-chloro-6-fluoro-1H-indazol-7-yl)cyclopentan-1-ol (50 mg,149.01 umol, 70.33% yield) was obtained as a white solid.

LCMS (electrospray) m/z 336.9 (M+H)+.

Intermediate 1N.4-bromo-6-fluoro-N-isopropyl-2-(tetrahydro-2H-pyran-2-yl)-5-(trifluoromethyl)-2H-indazol-7-amine

Step 1) 5-fluoro-2-iodo-4-(trifluoromethyl)aniline

To a solution of 3-fluoro-4-(trifluoromethyl)aniline (4 g, 22.33 mmol, 1eq) in MeCN (40 mL) was added NIS (5.53 g, 24.57 mmol, 1.1 eq) at 15°C., then reaction mixture was stirred at 15° C. for 15 h. The reactionmixture was diluted with H₂O (100 mL) and extracted with EtOAc (100mL*3). The combined organic layers were dried over Na₂SO₄, filtered andconcentrated under reduced pressure to give a residue.5-fluoro-2-iodo-4-(trifluoromethyl)aniline (5.6 g, crude) was obtainedas a brown oil.

LCMS (electrospray) m/z 305.9 (M+H)+.

Step 2) 5-fluoro-2-methyl-4-(trifluoromethyl)aniline

To a solution of 5-fluoro-2-iodo-4-(trifluoromethyl)aniline (6.0 g,19.67 mmol, 1 eq) and 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane(8.82 g, 29.51 mmol, 9.82 mL, 42% purity, 1.5 eq) in DME (60 mL) wereadded Pd(PPh₃)₄ (1.14 g, 983.57 umol, 0.05 eq) and K₂CO₃ (8.16 g, 59.01mmol, 3 eq) at 15° C., then reaction mixture was stirred at 100° C. for60 h. The reaction mixture was concentrated under reduced pressure toafford the residue. The residue was purified by column chromatography(SiO₂, Petroleum ether/Ethyl acetate=5/1 to 3/1, Petroleum ether/Ethylacetate=2:1, Rf=0.3). 5-fluoro-2-methyl-4-(trifluoromethyl)aniline (1.6g, 4.06 mmol, 20.64% yield, 49% purity) was obtained as a yellow oil.

LCMS (electrospray) m/z 194.1.9 (M+H)+.

Step 3) 6-fluoro-5-(trifluoromethyl)-1H-indazole

To a solution of 5-fluoro-2-methyl-4-(trifluoromethyl)aniline (1 g, 5.18mmol, 1 eq) in AcOH (15 mL) were added NaNO₂ (357.25 mg, 5.18 mmol, 1eq) and H₂O (3 mL) at 0° C., then the reaction mixture was stirred at15° C. for 2 h. The reaction was quenched by addition of H₂O (60 mL) at20° C. and the resulting mixture was extracted with EtOAc (50 mL*3). Thecombined organic layers were washed with H₂O (50 mL*3), dried overNa₂SO₄, filtered and concentrated under reduced pressure to give aresidue. Residue was purified by column (SiO2, Petroleum ether/Ethylacetate=10/1 to 5/1, Petroleum ether/Ethyl acetate=3:1, Rf=0.5).6-fluoro-5-(trifluoromethyl)-1H-indazole (500 mg, 2.45 mmol, 47.31%yield) was obtained as a yellow solid.

LCMS (electrospray) m/z 205.2 (M+H)+.

Step 4) 6-fluoro-7-nitro-5-(trifluoromethyl)-1H-indazole

To a solution of 6-fluoro-5-(trifluoromethyl)-1H-indazole (500 mg, 2.45mmol, 1 eq) in H₂SO₄ (5 mL, 95% purity) was added KNO₃ (249 mg, 2.46mmol, 1.01 eq) at 0° C., then the reaction mixture was stirred at 15° C.for 15 hr. The reaction mixture was diluted with water (100 mL) andextracted with Ethyl acetate (50 mL*2). The combined organic layers weretreated with saturated sodium bicarbonate solution until pH=7, driedover Na₂SO₄, filtered and concentrated under reduced pressure to give aresidue. 6-fluoro-7-nitro-5-(trifluoromethyl)-1H-indazole (500 mg) wasobtained as a yellow solid.

LCMS (electrospray) m/z 250.2 (M+H)+.

Step 5)6-fluoro-7-nitro-2-(tetrahydro-2H-pyran-2-yl)-5-(trifluoromethyl)-2H-indazole

To a solution of 6-fluoro-7-nitro-5-(trifluoromethyl)-1H-indazole (500mg, 2.01 mmol, 1 eq) in THF (10 mL) was added PPTS (50.44 mg, 200.71umol, 0.1 eq) and DHP (844.13 mg, 10.04 mmol, 917.53 uL, 5 eq) at 0° C.,then the reaction mixture was stirred at 60° C. for 15 hr. The reactionmixture was diluted with solvent H₂O (50 mL) and extracted with EtOAc(50 mL*3). The combined organic layers were washed with H₂O (50 mL*3),dried over Na₂SO₄, filtered and concentrated under reduced pressure togive a residue.6-fluoro-7-nitro-2-(tetrahydro-2H-pyran-2-yl)-5-(trifluoromethyl)-2H-indazole(1 g, crude) was obtained as yellow oil.

Step 6)6-fluoro-2-(tetrahydro-2H-pyran-2-yl)-5-(trifluoromethyl)-2H-indazol-7-amine

To a solution of6-fluoro-7-nitro-2-(tetrahydro-2H-pyran-2-yl)-5-(trifluoromethyl)-2H-indazole(800 mg, 2.40 mmol, 1 eq) and H₂O (2 mL) in EtOH (10 mL) was added NH₄Cl(642.08 mg, 12.00 mmol, 5 eq) and Fe (268.13 mg, 4.80 mmol, 2 eq) at 0°C., then the reaction mixture was stirred at 60° C. for 1 hr. Thereaction mixture was diluted with H₂O (20 mL) and extracted with EtOAc(20 mL*3). The combined organic layers were washed with H₂O (30 mL*2),dried over Na₂SO₄, filtered and concentrated under reduced pressure togive a residue. The residue was purified by column chromatography (SiO₂,Petroleum ether/Ethyl acetate=10/1 to 5/1, Petroleum ether:Ethylacetate=3:1, Rf=0.3).6-fluoro-2-(tetrahydro-2H-pyran-2-yl)-5-(trifluoromethyl)-2H-indazol-7-amine(500 mg, 1.65 mmol, 68.68% yield) was obtained as a yellow solid

LCMS (electrospray) m/z 220.2 (M+H)+.

Step 7)4-bromo-6-fluoro-2-(tetrahydro-2H-pyran-2-yl)-5-(trifluoromethyl)-2H-indazol-7-amine

To a solution of6-fluoro-2-(tetrahydro-2H-pyran-2-yl)-5-(trifluoromethyl)-2H-indazol-7-amine(200 mg, 659.51 umol, 1 eq) in DMF (1 mL) was added NBS (129.12 mg,725.46 umol, 1.1 eq) at 20° C., then the reaction mixture was stirred at20° C. for 2 hr. The reaction mixture was diluted with H₂O (10 mL) andextracted with EtOAc (10 mL*3). The combined organic layers were washedwith H₂O (10 mL*2), dried over Na₂SO₄, filtered and concentrated underreduced pressure to give a residue.4-bromo-6-fluoro-2-(tetrahydro-2H-pyran-2-yl)-5-(trifluoromethyl)-2H-indazol-7-amine(120 mg, crude) was obtained as a yellow solid.

LCMS (electrospray) m/z 297.9 (M+H)+.

Step 8)4-bromo-6-fluoro-N-isopropyl-5-(trifluoromethyl)-1H-indazol-7-amine

To a solution of4-bromo-6-fluoro-2-(tetrahydro-2H-pyran-2-yl)-5-(trifluoromethyl)-2H-indazol-7-amine(100 mg, 335.53 umol, 1 eq) in MeOH (1 mL) were added AcOH (40.30 mg,671.06 umol, 38.38 uL, 2 eq) and acetone (97.44 mg, 1.68 mmol, 123.34uL, 5 eq) at 20° C., NaBH₃CN (105.42 mg, 1.68 mmol, 5 eq) was then addedand the reaction mixture was stirred at 20° C. for 2 hr. After then,acetone (97.44 mg, 1.68 mmol, 123.34 uL, 5 eq), NaBH₃CN (105.43 mg, 1.68mmol, 5 eq) and AcOH (60.45 mg, 1.01 mmol, 57.57 uL, 3 eq) were added tothe mixture and the reaction mixture was stirred at 20° C. for 20 hr.The reaction mixture was diluted with H₂O (10 mL) and extracted withEtOAc (10 mL*3). The combined organic layers were washed with H₂O (10mL*2), dried over Na₂SO₄, filtered and concentrated under reducedpressure to give a residue. The residue was purified by prep-TLC(Petroleum ether:Ethyl acetate=3:1, Rf=0.4).4-bromo-6-fluoro-N-isopropyl-5-(trifluoromethyl)-1H-indazol-7-amine (60mg, 165.83 umol, 49.42% yield, 94% purity) was obtained as a whitesolid.

LCMS (electrospray) m/z 340.1 (M+H)+.

Step 9)4-bromo-6-fluoro-N-isopropyl-2-(tetrahydro-2H-pyran-2-yl)-5-(trifluoromethyl)-2H-indazol-7-amine

To a solution of4-bromo-6-fluoro-N-isopropyl-5-(trifluoromethyl)-1H-indazol-7-amine (50mg, 147.01 umol, 1 eq) in THF (1 mL) were added PPTS (3.69 mg, 14.70umol, 0.1 eq) and DHP (61.83 mg, 735.05 umol, 67.21 uL, 5 eq) at 0° C.,then the reaction mixture was stirred at 60° C. for 2 hr. The reactionmixture was diluted with H₂O (50 mL) and extracted with EtOAc (50 mL*3).The combined organic layers were washed with H₂O (50 mL*3), dried overNa₂SO₄, filtered and concentrated under reduced pressure to give aresidue. Residue was purified by prep-TLC (Petroleum ether:Ethylacetate=5:1, Rf=0.6).4-bromo-6-fluoro-N-isopropyl-2-(tetrahydro-2H-pyran-2-yl)-5-(trifluoromethyl)-2H-indazol-7-amine(50 mg, 117.86 umol, 80.17% yield) was obtained as a yellow oil.

LCMS (electrospray) m/z 424.1 (M+H)+.

Intermediate 10.4-bromo-5-cyclopropyl-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Step 1) 3-bromo-5-fluoro-2-methylaniline

To a mixture of 1-bromo-5-fluoro-2-methyl-3-nitrobenzene (23 g, 98.28mmol, 1 eq) in EtOH (80 mL) and H₂O (80 mL) was added Fe (27.44 g,491.41 mmol, 5 eq) and NH₄Cl (26.29 g, 491.41 mmol, 5 eq). The mixturewas stirred at 100° C. for 3 h. The mixture was filtered and thefiltrate was concentrated at reduced pressure to remove EtOH. Theresulting mixture was extracted with DCM (50 mL*3). The combined organicphase was washed with brine (50 mL*2), dried over Na₂SO₄, filtered andconcentrated at reduced pressure to give a residue to give3-bromo-5-fluoro-2-methylaniline (20.6 g, crude) as yellow liquid.

¹H NMR (400 MHz, DMSO-d₆) δ 6.59 (br d, J=8.4 Hz, 1H), 6.42 (br d,J=11.2 Hz, 1H), 5.51 (br s, 2H), 2.09 (s, 3H).

Step 2) 3-bromo-5-fluoro-4-iodo-2-methylaniline

To a mixture of 3-bromo-5-fluoro-2-methylaniline (18 g, 88.22 mmol, 1eq) (crude) in CH₃CN (150 mL) was added NIS (19.85 g, 88.22 mmol, 1 eq)in portions at 0° C. The mixture was stirred at 30° C. for 3 h. After 3h, LCMS showed compound 2 was remained and desired mass was detected,too. Then the mixture was stirred at 30° C. for another 12 h. LCMSshowed there was no compound 2 remained and one main peak with desiredmass was detected. The mixture was quenched with saturated Na₂SO₃ (200mL) and the resulting mixture was extracted with EtOAc (50 mL*3). Thecombined organic phase was washed with brine (50 mL*2), dried overNa₂SO₄, filtered and concentrated at reduced pressure to give a residue.The residue was purified by silica gel chromatography (1000 mesh silicagel, Petroleum ether/Ethyl acetate=50/1, 30/1; TLC (Petroleumether:Ethyl acetate=10:1; Rf=0.28)) to give3-bromo-5-fluoro-4-iodo-2-methylaniline (22 g, 66.68 mmol, 75.58% yield)as brown solid.

¹H NMR (400 MHz, DMSO-d₆) δ 6.55 (d, J=10.5 Hz, 1H), 5.67 (s, 2H), 2.25(d, J=0.8 Hz, 3H).

Step 3) 4-bromo-6-fluoro-5-iodo-1H-indazole

To a mixture of 3-bromo-5-fluoro-4-iodo-2-methylaniline (22 g, 66.68mmol, 1 eq) in CH₃COOH (200 mL) was added NaNO₂ (5.52 g, 80.02 mmol, 1.2eq) which was dissolved water (40 mL) at 0° C. The mixture was stirredat 30° C. for 16 h. The mixture was poured into saturated NaHCO₃ (1000mL) and the resulting mixture was extracted with EtOAc (200 mL*3). Thecombined organic phase was washed with brine (100 mL*2), dried overNa₂SO₄, filtered and concentrated at reduced pressure to give a residue.The residue was purified by silica gel chromatography (1000 mesh silicagel, Petroleum ether/Ethyl acetate=15/1, 5/1) to give4-bromo-6-fluoro-5-iodo-1H-indazole (7.5 g, 22.00 mmol, 32.99% yield) asbrown solid.

¹HNMR (400 MHz, DMSO-d₆) δ 13.58 (br s, 1H), 8.00 (s, 1H), 7.51 (d,J=8.1 Hz, 1H), 3.32 (s, 1H).

Step 4) 4-bromo-6-fluoro-5-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

To a mixture of 4-bromo-6-fluoro-5-iodo-1H-indazole (7.5 g, 22.00 mmol,1 eq) and 4-methylbenzenesulfonic acid; hydrate (418.47 mg, 2.20 mmol,0.1 eq) in DCM (100 mL) was added DHP (5.55 g, 66.00 mmol, 6.03 mL, 3eq) slowly. The mixture was stirred at 30° C. for 1 h. The mixture waswashed with saturated NaHCO₃ (30 mL*3) and brine (30 mL*3). The organicphase was dried over Na₂SO₄, filtered and concentrated at reducedpressure to give a residue. The residue was purified by silica gelchromatography (1000 mesh silica gel, Petroleum ether/Ethylacetate=100/1, 50/1) to give4-bromo-6-fluoro-5-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (7.4 g,17.41 mmol, 79.14% yield) as yellow solid.

¹H NMR (400 MHz, DMSO-d₆) δ 8.06 (s, 1H), 7.80 (dd, J=0.7, 8.4 Hz, 1H),5.83 (dd, J=2.4, 9.6 Hz, 1H), 3.88-3.85 (m, 1H), 3.80-3.70 (m, 2H),2.40-2.27 (m, 1H), 2.07-1.94 (m, 2H), 1.81-1.63 (m, 2H), 1.62-1.53 (m,2H).

Step 5)4-bromo-5-cyclopropyl-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

To a mixture of4-bromo-6-fluoro-5-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (1.5 g,3.53 mmol, 1 eq) and cyclopropylboronic acid (303.14 mg, 3.53 mmol, 1eq) in dioxane (10 mL) and H₂O (2.5 mL) was added Na₂CO₃ (748.10 mg,7.06 mmol, 2 eq) and Pd(dppf)Cl₂ (258.23 mg, 352.91 umol, 0.1 eq) underN₂. The mixture was stirred at 80° C. for 16 h. The mixture wasconcentrated at reduced pressure to give a residue. The residue waspurified by prep-TLC (Petroleum ether:Ethyl acetate=20:1) to give4-bromo-5-cyclopropyl-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole(0.21 g, 619.10 umol, 17.54% yield) as colorless oil.

¹H NMR (400 MHz, CDCl₃) δ 7.98 (d, J=0.6 Hz, 1H), 7.20 (d, J=10.4 Hz,1H), 5.61 (dd, J=2.8, 9.1 Hz, 1H), 4.03-3.94 (m, 1H), 3.76-3.69 (m, 1H),2.55-2.42 (m, 1H), 2.19-2.06 (m, 2H), 1.91-1.86 (m, 1H), 1.81-1.64 (m,3H), 1.12-1.05 (m, 2H), 0.87-0.81 (m, 2H).

Intermediate 1P. 4-bromo-6-fluoro-5-isopropyl-1H-indazole

Step 1)4-bromo-6-fluoro-5-(prop-1-en-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

To a mixture of4-bromo-6-fluoro-5-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (1.5 g,3.53 mmol, 1 eq) and potassium; trifluoro(isopropenyl)boranuide (626.67mg, 4.23 mmol, 1.2 eq) in dioxane (10 mL) and H₂O (2 mL) was addedPd(dppf)Cl₂ (258.23 mg, 352.91 umol, 0.1 eq) and Na₂CO₃ (748.10 mg, 7.06mmol, 2 eq) under N₂. The mixture was stirred at 80° C. for 16 h. Themixture was concentrated at reduced pressure to give a residue. Theresidue was purified by silica gel chromatography (1000 mesh silica gel,Petroleum ether/Ethyl acetate=100/1, 50/1; TLC (Petroleum ether:Ethylacetate=10:1; Rf=0.61)) to give 0.9 g of yellow oil. This oil waspurified by prep-TLC (Petroleum ether:Ethyl acetate=20:1) to give4-bromo-6-fluoro-5-(prop-1-en-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole(0.55 g, 1.62 mmol, 45.94% yield) as yellow oil.

¹H NMR (400 MHz, CDCl₃) δ 8.00 (d, J=0.6 Hz, 1H), 7.28 (d, J=0.9 Hz,0.5H), 7.26 (d, J=0.7 Hz, 0.5H), 5.64 (dd, J=2.8, 9.0 Hz, 1H), 5.46 (t,J=1.6 Hz, 1H), 5.01 (s, 1H), 4.05-3.97 (m, 1H), 3.80-3.69 (m, 1H),2.57-2.42 (m, 1H), 2.19-2.09 (m, 2H), 2.07 (s, 3H), 1.81-1.66 (m, 4H).

Step 2)4-bromo-6-fluoro-5-isopropyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

To a solution of4-bromo-6-fluoro-5-(prop-1-en-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole(0.4 g, 1.18 mmol, 1 eq) in MeOH (10 mL) was added PtO₂ under N₂. Thesuspension was degassed under vacuum and purged with H₂ several times.The mixture was stirred under H₂ (15 Psi) at 30° C. for 2.5 h. Themixture was filtered and the filtrate was concentrated at reducedpressure to give a residue The residue was purified by silica gelchromatography (300-400 mesh silica gel, Petroleum ether/Ethylacetate=50/1) to give4-bromo-6-fluoro-5-isopropyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole(0.3 g, 879.20 umol, 74.56% yield) as colorless oil.

Step 3) 4-bromo-6-fluoro-5-isopropyl-1H-indazole

To a solution of4-bromo-6-fluoro-5-isopropyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole(0.3 g, 879.20 umol, 1 eq) in DCM (1 mL) was added TFA (2.30 g, 20.14mmol, 1.49 mL, 22.91 eq). The mixture was stirred at 30° C. for 0.5 h.The mixture was concentrated at reduced pressure to give a residue. Theresidue was diluted with DCM (10 mL) and the resulting mixture wasadjusted pH to about 8 with TEA. The mixture was concentrated at reducedpressure to give a residue. The residue was purified by silica gelchromatography (300-400 mesh silica gel, Petroleum ether/Ethylacetate=30/1, 5/1) to give 4-bromo-6-fluoro-5-isopropyl-1H-indazole (0.2g, 777.90 umol, 88.48% yield) as colorless oil.

¹H NMR (400 MHz, CDCl₃) δ 8.04 (s, 1H), 7.11 (d, J=11.2 Hz, 1H),3.75-3.63 (m, 1H), 1.38 (dd, J=1.7, 7.1 Hz, 6H).

Intermediate 1Q. 4-bromo-6-fluoro-5-methoxy-1H-indazole

Step 1) 2-bromo-4-fluoro-3-methoxy-1-methylbenzene

To a solution of 2-bromo-6-fluoro-3-methylphenol (4.8 g, 23.41 mmol, 1eq) in acetone (50 mL) were added K₂CO₃ (6.47 g, 46.82 mmol, 2 eq) andiodomethane (9.97 g, 70.24 mmol, 4.37 mL, 3 eq), and the mixture wasstirred at 25° C. for 1 hour. The reaction mixture was concentrated togive a residue. The residue was dissolved in ethyl acetate (50 mL), andthe mixture was filtered, and the filtrate was concentrated to give aresidue (4.6 g, 21.00 mmol, 89.70% yield) as a yellow oil.

¹H NMR (400 MHz, CHLOROFORM-d) δ 7.05-6.85 (m, 2H), 3.95 (d, J=1.2 Hz,3H), 2.38 (s, 3H).

Step 2) 3-bromo-1-fluoro-2-methoxy-4-methyl-5-nitrobenzene

To a solution of 2-bromo-4-fluoro-3-methoxy-1-methylbenzene (4.4 g,20.09 mmol, 1 eq) in H₂SO₄ (40 mL) (98%) was added KNO₃ (2.23 g, 22.10mmol, 1.1 eq) in portions at 0° C., and the mixture was stirred at 25°C. for 1 hour. The reaction mixture was poured slowly into ice water(200 mL), then the mixture was extracted with ethyl acetate (200 mL*2),the combined organic layers were dried over Na₂SO₄, filtered andconcentrated under reduced pressure to give a residue.3-bromo-1-fluoro-2-methoxy-4-methyl-5-nitrobenzene (4.6 g, crude) wasobtained as a brown oil.

¹H NMR (400 MHz, CHLOROFORM-d) δ 7.70 (d, J=10.9 Hz, 1H), 4.08 (d, J=2.7Hz, 3H), 2.61 (d, J=1.1 Hz, 3H).

Step 3) 3-bromo-5-fluoro-4-methoxy-2-methylaniline

To a solution of 3-bromo-1-fluoro-2-methoxy-4-methyl-5-nitrobenzene (4.6g, 17.42 mmol, 1 eq) in EtOH (30 mL) and H₂O (30 mL) were added Fe (5.84g, 104.53 mmol, 6 eq) and NH₄Cl (5.59 g, 104.53 mmol, 6 eq), and themixture was stirred at 80° C. for 2 hours. The reaction mixture wasfiltered, and the filtrate was concentrated to remove EtOH, then themixture was diluted with EA (50 mL), and the mixture was washed withwater (20 mL*2), after then the organic layer was dried over Na₂SO₄,filtered and concentrated under reduced pressure to give a residue.3-bromo-5-fluoro-4-methoxy-2-methylaniline (3.5 g, crude) was obtainedas a brown oil.

¹H NMR (400 MHz, CHLOROFORM-d) δ 6.44 (d, J=11.9 Hz, 1H), 3.83 (s, 3H),3.76-3.48 (m, 2H), 2.24 (d, J=1.0 Hz, 3H).

Step 4) 4-bromo-6-fluoro-5-methoxy-1H-indazole

To a mixture of 3-bromo-5-fluoro-4-methoxy-2-methylaniline (3.5 g, 14.95mmol, 1 eq) (crude) in AcOH (20 mL) was added a solution of NaNO₂ (1.24g, 17.94 mmol, 1.2 eq) in H₂O (4 mL) dropwise at 0° C., then the mixturewas stirred at 25° C. for 12 hr. The reaction mixture was diluted withice water (100 mL), and the mixture was adjusted to pH 7 by using KOH,then the mixture was extracted with EA (100 mL*2), the combined organiclayers were washed with brine (50 mL*2), dried over Na₂SO₄, filtered andconcentrated under reduced pressure to give a residue. The residue waspurified by column chromatography (SiO₂, Petroleum ether/Ethylacetate=20/1 to 15:1). 4-bromo-6-fluoro-5-methoxy-1H-indazole (600 mg,2.45 mmol, 16.37% yield) was obtained as a brown solid.

¹H NMR (400 MHz, DMSO-d₆) δ 13.44 (br s, 1H), 8.00 (s, 1H), 7.52 (br d,J=10.4 Hz, 1H), 3.84 (s, 3H).

Synthesis of Formula (I) Compounds

Synthetic methods A to J were used to prepare the compounds of thefollowing. Below, the illustrating synthetic examples of some compoundsof the present disclosure are described, and other compounds can beprepared by the similar method to the one described below with differentstarting or reacting materials.

Synthetic Method A Example 2.(1S,2S)-2-fluoro-N-(6-(5-methyl-1H-indazol-4-yl)benzo[d]thiazol-2-yl)cyclopropane-1-carboxamide

To a solution of Compound 1 (0.2 g, 0.462 mmol, 1 eq)(5-methyl-1H-indazol-4-yl)boronic acid (0.081 g, 0.462 mmol, 1 eq) indioxane (4 mL) and H₂O (1 mL) was added Na₂CO₃ (0.146 g, 1.38 mmol, 3eq) and Pd(dppf)Cl₂ (33 mg, 0.046 mmol, 0.1 eq). The mixture was stirredat 110° C. for 16 hr. The reaction mixture was diluted with water (10mL) and extracted with ethyl acetate (10 mL×2). The combined organiclayers were dried over Na₂SO₄, filtered and concentrated under reducedpressure to give a residue. The residue was purified by columnchromatography to get Example 2 (135 mg, 0.369 mmol, 80% yield) wasobtained as a yellow solid.

¹H NMR (400 MHz, DMSO-d₆) δ 13.04 (s, NH), 12.76 (s, CONH), 8.05 (s,1H), 7.86 (d, J=8.0 Hz, 1H), 7.63 (s, 2H), 7.49-7.44 (m, 2H), 7.31 (d,J=8.4 Hz, 1H), 5.05 (td, J12=3.3 Hz, J13=65.7 Hz, 1H), 2.24 (s, 3H),2.23-2.24 (m, 1H), 1.78-1.73 (m, 1H), 1.31-1.23 (m, 1H); LCMS(electrospray) m/z 367.1 (M+H)+.

Synthetic Method B Example 58.(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(methylthio)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide.2 TFA

Step 1)(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(methylthio)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1l-carboxamide

To a solution of Compound 3 (4.4 g, 11.59 mmol, 1 eq) in dioxane (100mL) and H₂O (20 mL) was added Compound 2 (4.20 g, 11.59 mmol, 1 eq),Pd(dppf)Cl₂ (847.97 mg, 1.16 mmol, 0.1 eq) and Na₂CO₃ (2.46 g, 23.18mmol, 2 eq) under N₂. The reaction mixture was stirred at 90° C. for 12hr. Water (100 mL) was added and the aqueous phase was extracted with EA(200 mL*2). The combined organic phase was washed with saturated brine(200 mL*2), and concentrated in vacuum. The mixture was purified bycolumn chromatography on silica gel (Petroleum ether:Ethyl acetate=10:1to 1:1) to give product. Compound 4 (3.9 g, 7.29 mmol, 62.90% yield) asa light yellow solid.

¹H NMR (400 MHz, DMSO-d₆) δ 8.00-7.95 (m, 2H), 7.92-7.85 (m, 1H), 7.59(dd, J=1.8, 8.4 Hz, 1H), 5.70 (dd, J=2.5, 9.5 Hz, 1H), 5.07-4.79 (m,1H), 3.82-3.63 (m, 1H), 2.72 (d, J=0.9 Hz, 3H), 2.35-2.23 (m, 1H),2.04-1.94 (m, 2H), 1.81-1.48 (m, 4H), 1.46-1.33 (m, 2H).

Step 2)(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(methylthio)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide.2 TFA salt

To a solution of Compound 4 (3.80 g, 7.10 mmol, 1 eq) in DCM (100 mL)was added TFA (9.86 g, 86.51 mmol, 6.41 mL, 12.18 eq) under N₂. Thereaction mixture was stirred at 20° C. for 4 hr. DCM (10 ml) was added,Then the MeOH (200 ml) was slowly added. The reaction mixture wasstirred at 20° C. for 0.5 hr. The reaction mixture was filtered and thefilter cake was concentrated to give product. The filtrate wasconcentrated in vacuum to give product. Then the crude product waslyophilized to afford Example 58 (3.1 g, 4.26 mmol, 59.98% yield, 2 TFA)as a light yellow solid.

¹H NMR (400 MHz, DMSO-d₆) δ 13.76 (br s, 1H), 12.82 (br s, 1H), 8.19 (d,J=1.7 Hz, 1H), 7.96-7.82 (m, 2H), 7.59 (dd, J=1.8, 8.4 Hz, 1H),5.26-4.85 (m, 1H), 2.57 (s, 3H), 2.30-2.19 (m, 1H), 1.84-1.69 (m, 1H),1.33 (tdd, J=6.4, 9.0, 12.9 Hz, 1H); LCMS (electrospray) m/z 450.8(M+H)+.

Synthetic Method C Example 149.(1S,2S)—N-(5-(5-chloro-7-ethoxy-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide.2 TFA

Step 1)(1S,2S)-2-fluoro-N-(5-(tributylstannyl)thiazolo[5,4-b]pyridin-2-yl)cyclopropane-1-carboxamide

To a solution of Compound 5 (2.5 g, 7.91 mmol, 1 eq) in dioxane (30 mL)was added (SnBu₃)₂ (6.88 g, 11.86 mmol, 5.93 mL, 1.5 eq), Pd(PPh₃)₄(913.78 mg, 790.77 umol, 0.1 eq) and LiCl (1.01 g, 23.72 mmol, 485.85uL, 3 eq). The mixture was stirred at 110° C. for 16 hr under N₂atmosphere. The reaction mixture was filtered and the filtrate wasconcentrated under reduced pressure to give a residue. The residue waspurified by column chromatography (Silical gel, Petroleum ether:Ethylacetate=10:1 to 3:1). Compound 6 (1.3 g, 2.47 mmol, 31.24% yield) wasobtained as a yellow oil.

Step 2)(1S,2S)—N-(5-(5-chloro-7-ethoxy-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide.2 TFA

To a solution of 4-bromo-5-chloro-7-ethoxy-6-fluoro-1H-indazole (100 mg,264.81 umol, 1 eq) in dioxane (2 mL) were added Compound 6 (167.24 mg,317.77 umol, 1.2 eq), Pd(PPh₃)₄ (30.60 mg, 26.48 umol, 0.1 eq) and LiCl(33.68 mg, 794.42 umol, 16.27 uL, 3 eq). The mixture was stirred at 140°C. for 2 hr under microwave. After then, the reaction mixture was addedwith saturated K₂CO₃ aqueous 10 mL and stirred at 20° C. for 15 min. Themixture was diluted with water 10 mL and extracted with Ethyl acetate(20 mL*2). The combined organic layers were washed with brine (20 mL*2),dried over Na₂SO₄, filtered and the filtrate was concentrated underreduced pressure to give a residue. The residue was purified by prep-TLC(Silical gel plate, Petroleum ether:Ethyl acetate=1:2) to give a crudeproduct. The crude product was purified by prep-HPLC (column: Phenomenexluna C18 150*25 mm*10 um; mobile phase: [water (0.1% TFA)-ACN]; B %:55%-85%, 10 min). Example 149 (60 mg, 112.36 umol, 42.43% yield) wasobtained as a yellow oil.

¹H NMR (400 MHz, DMSO-d₆) δ 12.97 (s, 1H), 8.28 (d, J=8.4 Hz, 1H), 7.95(s, 1H), 7.81 (d, J=8.4 Hz, 1H), 6.12-6.06 (m, 1H), 5.20-4.96 (m, 1H),4.46-4.34 (q, J=7.0 Hz, 2H), 3.97 (m, 1H), 3.73-3.61 (m, 1H), 2.47-2.40(m, 1H), 2.32-2.22 (m, 1H), 2.04 (m, 2H), 1.83-1.69 (m, 2H), 1.57 (m,2H), 1.49 (t, J=7.0 Hz, 3H), 1.41-1.28 (m, 1H).

Synthetic Method D Example 152.(1S,2S)—N-(5-(5-ethyl-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide

To a solution of Intermediate 1K (45 mg, 185.13 umol, 1 eq) in EtOH (2mL) were added Compound 6 (116.92 mg, 222.15 umol, 1.2 eq) andAd₂nBuP-Pd-G3 (13.48 mg, 18.51 umol, 0.1 eq). The mixture was stirred at80° C. for 16 hr under N₂ atmosphere. The reaction mixture was dilutedwith water 20 mL and extracted with Ethyl acetate (20 mL*2). Thecombined organic layers were washed with brine (20 mL*2), dried overNa₂SO₄, filtered and the filtrate was concentrated under reducedpressure to give a residue. The residue was purified by prep-HPLC(column: Phenomenex luna C18 150*25 mm*10 um; mobile phase: [water (0.1%TFA)-ACN]; B %: 33%-63%, 10 min) to give a crude product. The crudeproduct was purified by prep-TLC (Silical gel plate, Petroleumether:Ethyl acetate=1:1). Example 152 (9.7 mg, 24.29 umol, 13.12% yield,100% purity) was obtained as a white solid.

¹H NMR (400 MHz, DMSO-d₆) δ 13.18 (br s, 1H), 12.94 (br s, 1H), 8.26 (d,J=8.2 Hz, 1H), 7.72 (s, 1H), 7.68 (d, J=8.3 Hz, 1H), 7.42 (d, J=10.1 Hz,1H), 5.20-4.95 (m, 1H), 2.65 (dq, J=2.4, 7.2 Hz, 2H), 2.27 (m, 1H),1.85-1.69 (m, 1H), 1.34 (m, 1H), 1.11 (t, J=7.0 Hz, 3H); LCMS(electrospray) m/z 400.4 (M+H)+.

Synthetic Method E Example 221.(1S,2S)-2-fluoro-N-(6-(5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide

Step 1)(1S,2S)-2-fluoro-N-(6-iodoimidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide

A mixture of Compound 7 (5.890 g, 22.737 mmol),(1S,2S)-2-fluorocyclopropane-1-carboxylic acid (3.076 g, 29.558 mmol)and 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride(EDC-HCl, 6.538 g, 34.105 mmol) in dichloromethane (100 mL) was treatedat the room temperature with N,N-diisopropylethylamine (2.376 mL, 13.642mmol), stirred at the same temperature for 40 hr. The precipitates werecollected by filtration, washed by dichloromethane, and dried to giveCompound 8 as beige solid (3.870 g, 49.3%).

¹H NMR (400 MHz, DMSO-d₆) δ 10.99 (s, 1H), 8.87 (s, 1H), 8.02 (s, 1H),7.36˜7.23 (m, 2H), 4.97˜4.77 (m, 1H), 2.09˜2.07 (m, 1H), 1.65˜1.57 (m,1H), 1.16˜1.09 (m, 1H).

Step 2)(1S,2S)-2-fluoro-N-(6-(5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide

Compound 8 (0.750 g, 2.173 mmol), (5-methyl-1H-indazol-4-yl)boronic acid(0.459 g, 2.608 mmol),[1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)(Pd(dppf)Cl₂, 0.159 g, 0.217 mmol) and cesium carbonate (1.416 g, 4.346mmol) in tetrahydrofuran (15 mL)/water (4 mL) was mixed at the roomtemperature and then heated at 120° C. under the microwaves for 1 hr,cooled down to the room temperature, filtered through a celite pad toremove solids, and partitioned between ethyl acetate and saturatedaqueous sodium bicarbonate solution. The organic layer was washed withaqueous saturated sodium chloride solution, separated, dried (anhydrousMgSO4), filtered, and concentrated in vacuo. The residue waschromatographed (SiO₂, 30 g cartridge; ethyl acetate/hexane=100%) togive the crude product which was crystallized at the room temperatureusing diethylether (5 mL). The resulting precipitates were filtered,washed by diethylether, and dried to give Example 221 as light yellowsolid (0.550 g, 72.4%).

¹H NMR (400 MHz, DMSO-d₆) δ 12.77 (s, 1H), 9.70 (s, 1H), 9.00 (s, 1H),8.66 (d, J=9.2 Hz, 1H), 8.59 (s, 1H), 8.55 (d, J=9.2 Hz, 1H), 8.33 (d,J=8.0 Hz, 1H), 8.14 (d, J=8.8 Hz, 1H), 5.91˜5.71 (m, 1H), 3.11 (s, 3H),3.05˜3.00 (m, 1H), 2.54˜2.48 (m, 1H), 2.07˜2.03 (m, 1H); LCMS(electrospray) m/z 350.0 (M+H)+.

Synthetic Method F Example 223.N-(6-(5-chloro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide.dihydrochloride

Step 1) (2-amino-6-iodoimidazo[1,2-a]pyridin-3-yl)(cyclopropyl)methanone

To a solution of cyclopropanecarboxylic acid (3.17 g, 36.78 mmol, 2.91mL, 1.3 eq) in DCM (50 mL) was added EDCI (6.51 g, 33.95 mmol, 1.2 eq),HOBt (4.59 g, 33.95 mmol, 1.2 eq) and TEA (8.59 g, 84.89 mmol, 11.82 mL,3 eq). The mixture was stirred at 20° C. for 1 hr. then added Compound 7(6 g, 28.30 mmol, 1 eq). The final mixture was stirred at 20° C. for 18hr. The mixture was poured into H₂O (200 mL) and extracted with Ethylacetate (300 mL*3), the organic phase was washed with brine (500 mL*2)and dried with anhydrous sodium sulfate (Na₂SO₄), filtered andconcentrated in vacuum. The residue was purified by trituration withEthyl acetate (50 mL), filtered and the filter cake was concentrated.Compound 9 (1.9 g, 6.78 mmol, 23.96% yield) was obtained as yellowsolid.

¹H NMR (400 MHz, DMSO-d₆) δ 9.70 (d, J=1.2 Hz, 1H), 7.60 (dd, J=2.1, 9.3Hz, 1H), 7.32 (d, J=9.3 Hz, 1H), 6.62 (s, 2H), 2.46-2.37 (m, 1H),1.02-0.90 (m, 4H).

Step 2)(1S,2S)-2-fluoro-N-(6-(5-methyl-1H-indol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamidedihydrochloride

To a solution of Compound 9 (10.22 g, 31.27 mmol, 1 eq) and4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane(11.12 g, 43.78 mmol, 1.4 eq) in dioxane (100 mL) was added KOAc (9.21g, 93.82 mmol, 3 eq) and Pd(dppf)Cl₂ (1.14 g, 1.56 mmol, 0.05 eq). Themixture was heated to 90° C. for 3 hr. The residue was poured into water(200 mL). The aqueous phase was extracted with ethyl acetate (200 mL*2).The combined organic phase was washed with brine (300 mL), dried withanhydrous Na₂SO₄, filtered and concentrated in vacuum. TLC (Petroleumether/Ethyl acetate=0:1) showed a main spot. The residue was purified bysilica gel chromatography eluted with Petroleum ether/Ethyl acetate=0:1.Compound 10 (11 g, crude) was obtained as yellow solid. The crude waspurified by triturated with Petroleum ether (20 mL) and Ethyl acetate (4mL), filtered and the filter cake was concentrated. Compound 10 (6.3 g,19.26 mmol, 48.46% yield) was obtained as white solid.

Step 3)N-(6-(5-chloro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide.Dihydrochloride

To a solution of Compound 10 (100 mg, 305.64 umol, 1 eq) and4-bromo-5-chloro-1H-indazole (84.90 mg, 366.76 umol, 1.2 eq) in dioxane(3 mL) and H₂O (1 mL) was added Na₂CO₃ (97.18 mg, 916.91 umol, 3 eq) andPd(dppf)Cl₂ (11.18 mg, 15.28 umol, 0.05 eq). The mixture was stirred at90° C. for 10 hr. The mixture was poured into Petroleum ether (10 mL),filtered with silica gel and the filtrate was concentrated in vacuum.The residue was purified by prep-HPLC (column: Phenomenex Synergi C18150*25*10 um; mobile phase: [water (0.05% HCl)-ACN]; B %: 14%-34%, 9min), followed by lyophilization. Example 223 (36.8 mg, 85.95 umol,28.12% yield, 99.2% purity, 2 HCl) was obtained as white solid.

¹H NMR (400 MHz, METHANOL-d₄) δ 8.92 (s, 1H), 8.13 (s, 1H), 7.99-7.91(m, 3H), 7.68 (dd, J=1.0, 8.9 Hz, 1H), 7.58 (d, J=8.9 Hz, 1H), 1.95-1.87(m, 1H), 1.12-1.07 (m, 2H), 1.05-0.98 (m, 2H); LCMS (electrospray) m/z352.0 (M+H)+.

Synthetic Method G Example 231.N-(6-(5-bromo-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide.2 TFA salt

A mixture of CuBr (137.29 mg, 957.04 umol, 29.15 uL, 1 eq) and t-BuONO(98.69 mg, 957.04 umol, 113.83 uL, 1 eq) in MeCN (5 mL) was stirred at0° C. for 30 mins, after then a solution of Example 227 (662 mg, 957.04umol, 1 eq) in MeCN (1 mL) was added, and the mixture was stirred at 20°C. for 2 hours, after then CuBr (137.29 mg, 957.04 umol, 29.15 uL, 1 eq)and t-BuONO (98.69 mg, 957.04 umol, 113.83 uL, 1 eq) were added, and themixture was stirred at 20° C. for another 12 hours. The reaction mixturewas concentrated to give a residue, then the residue was dissolved inethyl acetate (50 mL), after then the mixture was washed with dilutedammonium hydroxide (3%, 20 mL*2), the organic layer was washed withbrine (20 mL), dried over Na₂SO₄, filtered and concentrated underreduced pressure to give a residue. The residue was purified byprep-HPLC (column: Phenomenex Synergi C18 150*25*10 um; mobile phase:[water (0.1% TFA)-ACN]; B %: 20%-50%, 9 min). Example 231 (14 mg, 22.01umol, 2.3% yield, 2TFA) was obtained as a yellow solid.

¹H NMR (400 MHz, DMSO-d₆) δ 13.49 (br s, 1H), 11.05 (s, 1H), 8.78 (s,1H), 8.14 (s, 1H), 7.92 (s, 1H), 7.64 (d, J=8.7 Hz, 1H), 7.57 (d, J=9.2Hz, 1H), 7.32 (dd, J=1.7, 9.2 Hz, 1H), 2.05-1.86 (m, 1H), 0.85-0.79 (m,4H); LCMS (electrospray) m/z 414.1 (M+H)+.

Synthetic Method H Example 258.(1S,2S)—N-(6-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide

Step 1)(1S,2S)—N-(6-(5-chloro-7-(dimethylamino)-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide

To a solution of Intermediate 1D (30 mg, 78.06 umol, 1 eq) and Compound11 (32.33 mg, 93.67 umol, 1.2 eq) in dioxane (1 mL) and H₂O (0.2 mL)were added Pd(dppf)Cl₂ (5.71 mg, 7.81 umol, 0.1 eq) and Na₂CO₃ (24.82mg, 234.17 umol, 3 eq), then the mixture was stirred at 80° C. for 12hours under N₂. The reaction mixture was concentrated to give a residue.The residue was purified by prep-TLC (SiO₂,Dichloromethane:Methanol=10:1). Compound 12 (34 mg, 57.44 umol, 73.59%yield, 87% purity) was obtained as a yellow oil.

Step 2)(1S,2S)—N-(6-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide

To a solution of Compound 12 (34 mg, 57.44 umol, 1 eq) in dioxane (1 mL)was added HCl/dioxane (4 M, 1 mL, 69.64 eq), then the mixture wasstirred at 20° C. for 2 hours under N₂. The reaction mixture was dilutedwith ethyl acetate (20 mL), and the mixture was washed with saturatedaqueous solution of NaHCO₃ (15 mL*2), the organic layer was dried overNa₂SO₄, filtered and concentrated under reduced pressure to give aresidue. The residue was purified by prep-HPLC (column: Phenomenex lunaC₁₈ 150*25 10u; mobile phase: [water (0.1% TFA)-ACN]; B %: 23%-53%, 10min). Example 258 (8.7 mg, 13.05 umol, 22.72% yield, 2 TFA) was obtainedas a white solid.

¹H NMR (400 MHz, DMSO-d₆) δ 13.55 (br s, 1H), 11.21 (s, 1H), 8.80 (s,1H), 8.17 (s, 1H), 7.95 (s, 1H), 7.62 (d, J=9.2 Hz, 1H), 7.43 (d, J=9.2Hz, 1H), 5.08-4.77 (m, 1H), 3.01 (s, 3H), 3.00 (s, 3H), 2.16 (td, J=7.0,13.8 Hz, 1H), 1.76-1.57 (m, 1H), 1.27-1.11 (m, 1H); LCMS (electrospray)m/z 431.2 (M+H)+.

Synthetic Method I Example 393.(1S,2S)—N-(6-(7-(1-(2H-tetrazol-2-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide

Step 1)1-(4-bromo-5-chloro-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-7-yl)ethan-1-one

To a solution of Intermediate 1A (3.29 g, 9.86 mmol, 1 eq) in THF (49mL) was cooled to −78° C. then, LDA (7.39 mL, 14.7 mmol, 1.5 eq) wasadded slowly to reaction mixture, stirred at the same temperature for 30min. Then acetic anhydride (1.11 mL, 11.8 mmol, 1.2 eq) was addeddropwise and the reaction mixture was stirred at rt for 2 hrs. After theIntermediate 1A was consumed, quenched with water and extracted withDCM, separated, dried over anhydrous MgSO₄, filtered, and concentratedin vacuo. The residue was purified by silica gel chromatography (productcame out at Hexane/Ethyl acetate=10/1) to afford Compound 13 (1.86 g,4.95 mmol, 50.2% yield) as an orange solid.

Step 2)1-(4-bromo-5-chloro-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-7-yl)ethan-1-ol

To a solution of Compound 13 (1.86 mg, 4.95 mmol, 1 eq) in MeOH (24 mL)were cooled to 0° C. then sodium borohydride (375 mg, 9.90 mmol, 2 eq)was added portionwise. The reaction mixture was stirred at rt for 2 hrs.After the Compound 13 was consumed, the reaction mixture wasconcentrated and extracted with DCM, washed with water, separated, driedover anhydrous MgSO₄, filtered, and concentrated in vacuo. The residuewas purified by silica gel chromatography (product came out atHexane/Ethyl acetate=7/3) to afford Compound 14 (615 mg, 1.62 mmol, 32%yield) as an ivory solid.

Step 3)7-(1-(2H-tetrazol-2-yl)ethyl)-4-bromo-5-chloro-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

To a solution of Compound 14 (100 mg, 0.265 mmol, 1.0 eq) in THF (1.33mL) was added 1H-tetrazole (0.89 mL, 0.398 mmol, 1.5 eq) and PPh₃ (104mg, 0.398 mmol, 1.5 eq). The mixture was cooled to 0° C. and DEAD (0.181mL, 0.398 mmol, 1.5 eq) was added slowly at 0° C. The mixture wasstirred at room temperature for 1 hr. The reaction mixture was extractedwith DCM (30 mL*3). The combined organic layers were dried over Na₂SO₄,filtered and the filtrate was concentrated in vacuum. The crude productwas purified by silica gel chromatography (product came out Hexane/Ethylacetate=10/2) to afford Compound 15 (62 mg, 0.144 mmol, 54% yield) as awhite color solid.

Step 4)(1S,2S)—N-(6-(7-(1-(2H-tetrazol-2-yl)ethyl)-5-chloro-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide

To a solution of Compound 15 (62 mg, 0.144 mmol, 1 eq) in 1,4-Dioxane(0.577 mL)/H₂O (0.144 mL) were added Compound 11 (54 mg, 0.159 mmol, 1.1eq), Pd(dppf)Cl₂ (5 mg, 0.007 mmol, 0.05 eq), Na₂CO₃ (30 mg, 0.289 mmol,2 eq). The mixture was degassed and purged with N₂ for 3 times. Themixture was stirred at 120° C. for 30 min in microwave reactor. Thereaction mixture was filtered through celite and filtrate was extractedwith DCM. The combined organic layers were dried over Na₂SO₄, filteredand the filtrate was concentrated in vacuum to give a residue. Theresidue was purified by silica gel chromatography (product came out atHexane/Ethyl acetate=2/8) to afford Compound 16 (68 mg, 0.120 mmol, 83%)as a yellow solid.

Step 5)(1S,2S)—N-(6-(7-(1-(2H-tetrazol-2-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide

To a solution of Compound 16 (66 mg, 0.116 mmol, 1 eq) in Ethyl acetate(0.6 mL) was added 1 N HCl in EA solution (1.16 mL, 1.16 mmol, 10 eq).The mixture was stirred at room temperature for 1 hr. The reactionmixture was quenched by saturated NaHCO₃ and extracted with EA, driedover Na₂SO₄, filtered and the filtrate was concentrated in vacuum. Thecrude product was purified by silica gel chromatography (product cameout at DCM/MeOH=10/1) to afford Example 393 (4 mg, 0.008 mmol, 7%) as anivory solid.

¹H NMR (400 MHz, DMSO-d₆) δ 13.77 (s, 1H), 11.07 (s, 1H), 8.99 (s, 1H),8.80 (s, 1H), 8.14-8.04 (m, 2H), 7.58-7.54 (m, 1H), 7.35 (dd, J=9.3, 1.6Hz, 1H), 6.74 (q, J=7.1 Hz, 1H), 5.00-4.79 (m, 1H), 2.23 (d, J=7.2 Hz,3H), 2.16-2.09 (m, 1H), 1.68-1.57 (m, 1H), 1.18-1.09 (m, 1H)); LCMS(electrospray) m/z 485.10 (M+H)+.

Synthetic Method J Example 446.(1S,2S)-2-fluoro-N-(5-(5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

Step 1)(1S,2S)—N-(5-bromopyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide

To a mixture of Compound 17 (3.1 g, 14.62 mmol, 1 eq) and(1S,2S)-2-fluorocyclopropanecarboxylic acid (1.67 g, 16.08 mmol, 1.1 eq)in CH₃CN (40 mL) was added MsCl (3.35 g, 29.24 mmol, 2.26 mL, 2 eq) and3-methylpyridine (6.81 g, 73.10 mmol, 7.12 mL, 5 eq) slowly at 0° C.under N₂. The mixture was stirred at 30° C. for 3 h. The mixture wasconcentrated at reduced pressure. The residue was dissolved with ethylacetate (200 mL) and the resulting mixture was washed with 10% citricacid (30 mL*2), saturated Na₂CO₃ (30 mL*2), brine (30 mL*2), dried overNa₂SO₄, filtered and concentrated at reduced pressure to give a residue.The residue was purified by silica gel chromatography (1000 mesh silicagel, Petroleum ether/Ethyl acetate=5/1, 3/1) to give Compound 18 (2.3 g,7.72 mmol, 52.81% yield) as white solid.

Step 2)(1S,2S)-2-fluoro-N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropane-1-carboxamide

Compound 18 (0.345 g, 1.159 mmol),4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane, 0.588 g,2.318 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)(Pd(dppf)Cl₂, 0.084 g, 0.115 mmol) and potassium acetate (0.398 g, 4.056mmol) were mixed at the room temperature in DMSO (10 mL) and thenstirred at 90° C. for 18 h, cooled down to the room temperature,filtered through a celite pad to remove solids, and partitioned betweenethyl acetate and water. The organic layer was washed with aqueoussaturated sodium chloride solution, separated, dried with anhydrousMgSO₄, filtered, and concentrated in vacuo. The residue waschromatographed (SiO₂, 12 g cartridge; ethyl acetate/hexane=0% to 100%)to give Compound 19 as brown solid (0.289 g, 72.3%).

Step 3)(1S,2S)-2-fluoro-N-(5-(5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

To a mixture of Compound 19 (6 g*, 17.34 mmol, 1 eq) and4-bromo-5-methyl-1H-indazole (3.6 g, 17.34 mmol, 1 eq) in dioxane (120mL) and H₂O (24 mL) was added Na₂CO₃ (3.67 g, 34.68 mmol, 2 eq) andPd(dppf)Cl₂ (1.28 g, 1.73 mmol, 0.1 eq) under N₂. The mixture wasstirred at 90° C. for 4 h. The mixture was concentrated at reducedpressure to give a residue. The residue was purified by silica gelchromatography (1000 mesh silica gel, Petroleum ether/Ethyl acetate=5/1,1/1; TLC (Petroleum ether:Ethyl acetate=1:1; Rf=0.08) to give 2.5 g ofyellow solid. This solid was triturated with CH₃CN (10 mL) for twotimes. The mixture was filtered and the filtered cake was collected. Thecake was dispersed with H₂O/CH₃CN (5:1; 10 mL) and the resulting mixturewas lyophilizated for third times to give Example 446 (1.53 g, 4.37mmol, 25.20% yield, 96.98% purity) as pale solid.

¹H NMR (400 MHz, DMSO-d₆) δ 13.09 (s, 1H), 11.13 (s, 1H), 8.61 (d, J=7.1Hz, 1H), 7.74 (s, 1H), 7.63 (d, J=0.9 Hz, 1H), 7.49 (d, J=8.6 Hz, 1H),7.32 (d, J=8.6 Hz, 1H), 6.91 (s, 1H), 6.86 (dd, J=1.9, 7.0 Hz, 1H),5.06-4.98 (m, 1H), 4.88-4.84 (m, 1H), 2.34 (s, 3H), 2.15 (td, J=6.9,13.8 Hz, 1H), 1.74-1.61 (m, 1H), 1.21-1.13 (m, 1H); LCMS (electrospray)m/z 350.1 (M+H)+.

Table 1 below shows the compounds of Examples along with generalsynthetic methods used to make the compound and characterization data.

TABLE 1 Compounds of Examples Meth- Ex # Structure/Name ¹H NMR/MS(M + 1) od 1

¹H NMR (400 MHz, DMSO-d₆) δ 13.04 (s, NH), 12.69 (s, CONH), 8.03 (s,1H), 7.84 (d, J = 8.4 Hz, 1H), 7.63 (s, 1H), 7.48-7.44 (m, 1H), 7.31 (d,J = 8.4 Hz, 1H), 2.30 (s, 3H), 2.02 (t, J = 5.6 Hz, 1H), 0.97 (t, J =4.0 Hz, 4H); LCMS (electrospray) m/z 349.0 (M + H)+. AN-(6-(5-methyl-1H-indazol-4- yl)benzo[d]thiazol-2-yl)cyclopropanecarboxamide 2

¹H NMR (400 MHz, DMSO-d₆) δ 13.04 (s, NH), 12.76 (s, CONH), 8.05 (s,1H), 7.86 (d, J = 8.0 Hz, 1H), 7.63 (s, 2H), 7.49-7.44 (m, 2H), 7.31 (d,J = 8.4 Hz, 1H), 5.05 (td, J12 = 3.3 Hz, J13 = 65.7 Hz, 1H), 2.24 (s,3H), 2.23-2.24 (m, 1H), 1.78-1.73 (m, 1H), 1.31-1.23 (m, 1H); LCMS(electrospray) m/z 367.1 (M + H)+. A (1S,2S)-2-fluoro-N-(6-(5-methyl-1H-indazol-4-yl)benzo[d]thiazol-2- yl)cyclopropane-1-carboxamide 3

¹H NMR (400 MHz, DMSO-d₆) δ 13.03 (s, 1H), 11.80 (s, 1H), 7.99 (s, 1H),7.78 (d, 8.4 Hz, 1H), 7.63 (s, 1H), 7.46-7.42 (m, 2H), 7.31 (d, 8.4 Hz,1H), 2.30 (s, 3H), 1.52 (s, 9H); LCMS (electrospray) m/z 381.1 (M + H)+.A tert-butyl (6-(5-methyl-1H-indazol-4-yl)benzo[d]thiazol-2-yl)carbamate 4

¹H NMR (400 MHz, DMSO-d₆) δ 13.02 (br s, 1H), 12.28 (br s, 1H), 8.04 (d,J = 1.3 Hz, 1H), 7.83 (d, J = 8.3 Hz, 1H), 7.63 (s, 1H), 7.50-7.43 (m,2H), 7.31 (d, J = 8.4 Hz, 1H), 3.44 (quin, J = 8.5 Hz, 1H), 2.32-2.13(m, 7H), 2.06-1.92 (m, 1H), 1.90-1.78 (m, 1H); LCMS (electrospray) m/z363.2 (M + H)+. A N-(6-(5-methyl-1H-indazol-4- yl)benzo[d]thiazol-2-yl)cyclobutanecarboxamide. 2 TFA 5

¹H NMR (400 MHz, DMSO-d₆) δ 13.21-12.83 (m, 2H), 8.08 (d, J = 1.2 Hz,1H), 7.89 (d, J = 8.3 Hz, 1H), 7.64 (s, 1H), 7.52-7.43 (m, 2H), 7.32 (d,J = 8.6 Hz, 1H), 3.02 (td, J = 9.5, 13.0 Hz, 1H), 2.30 (s, 3H),2.23-2.11 (m, 2H); LCMS (electrospray) m/z 385.0 (M + H)+. A2,2-difluoro-N-(6-(5-methyl-1H-indazol-4-yl)benzo[d]thiazol-2-yl)cyclopropane-1- carboxamide. 2 TFA salt 6

¹H NMR (400 MHz, DMSO-d₆) δ 13.05 (br s, 1H), 12.50 (s, 1H), 8.06 (d, J= 1.3 Hz, 1H), 7.85 (d, J = 8.3 Hz, 1H), 7.63 (s, 1H), 7.50-7.44 (m,2H), 7.32 (d, J = 8.6 Hz, 1H), 5.19-4.95 (m, 1H), 2.97- 2.85 (m, 1H),2.66-2.57 (m, 2H), 2.45-2.35 (m, 2H), 2.30 (s, 3H); LCMS (electrospray)m/z 381.1 (M + H)+. A (1S,3S)-3-fluoro-N-(6-(5-methyl-1H-indazol-4-yl)benzo[d]thiazol-2- yl)cyclobutane-1-carboxamide. 2 TFA 7

¹H NMR (400 MHz, DMSO-d₆) δ 13.03 (br s, 1H), 12.48 (s, 1H), 8.06 (d, J= 1.3 Hz, 1H), 7.85 (d, J = 8.3 Hz, 1H), 7.63 (s, 1H), 7.50-7.43 (m,2H), 7.32 (d, J = 8.6 Hz, 1H), 5.37-5.15 (m, 1H), 3.45 (br d, J = 3.1Hz, 1H), 2.65-2.55 (m, 2H), 2.45-2.35 (m, 2H), 2.30 (s, 3H); LCMS(electrospray) m/z 381.1 (M + H)+. A (1R,3R)-3-fluoro-N-(6-(5-methyl-1H-indazol-4-yl)benzo[d]thiazol-2- yl)cyclobutane-1-carboxamide. 2 TFA 8

¹H NMR (400 MHz, DMSO-d₆) δ 13.04(s, 1H), 12.93(s, 1H), 8.16(dd, J = 8.4Hz, J = 2.0 Hz, 2H), 8.10(s, 1H), 7.91(d, J = 7.6 Hz, 1H), 7.70-7.65(m,2H), 7.60-7.57(m, 2H), 7.53(dd, J = 8.4 Hz, 2.0 Hz, 1H), 7.47(d, J = 8.4Hz, 1H), 7.32(d, J = 8.8 Hz, 1H), 2.32(s, 3H); LCMS (electrospray) m/z385.1 (M + H)+. A N-(6-(5-methyl-1H-indazol-4-yl)benzo[d]thiazol-2-yl)benzamide 9

¹H NMR (400 MHz, DMSO-d₆) δ 12.99 (s, NH), 12.31 (s, NH), 7.99 (s, 1H),7.80 (d, J = 8.0 Hz, 1H), 7.58 (s, 1H), 7.44-7.40 (m, 2H), 7.27 (d, J =8.0 Hz, 1H), 2.26 (s, 3H), 1.59 (m, 2H), 1.31-1.29 (m, 2H), 0.89-0.85(m, 3H); LCMS (electrospray) m/z 365.1 (M + H)+. AN-(6-(5-methyl-1H-indazol-4- yl)benzo[d]thiazol-2-yl)pentanamide 10

¹H NMR (400 MHz, DMSO-d₆) δ 12.98 (s, NH), 12.32 (s, NH), 7.99 (s, 1H),7.80 (d, J = 8.0 Hz, 1H), 7.58 (s, 1H), 7.44-7.40 (m, 2H), 7.27 (d, J =8.0 Hz, 1H), 2.96 (m, 1H), 2.26 (s, 3H), 1.89 (m, 2H), 1.79-1.49 (m,4H), 1.24-1.20 (m, 1H), 0.83- 0.80 (m, 1H); LCMS (electrospray) m/z377.1 (M + H)+. A N-(6-(5-methyl-1H-indazol-4- yl)benzo[d]thiazol-2-yl)cyclopentanecarboxamide 11

¹H NMR (400 MHz, DMSO-d₆) δ 13.08 (br s, 1H), 12.60 (br s, 1H), 8.07 (d,J = 1.3 Hz, 1H), 7.86 (d, J = 8.2 Hz, 1H), 7.64 (s, 1H), 7.51-7.43 (m,2H), 7.32 (d, J = 8.6 Hz, 1H), 3.38-3.25 (m, 1H), 2.98- 2.81 (m, 4H),2.30 (s, 3H); LCMS (electrospray) m/z 377.1 (M + H)+. A3,3-difluoro-N-(6-(5-methyl-1H-indazol-4-yl)benzo[d]thiazol-2-yl)cyclobutane-1- carboxamide. 2 TFA 12

¹H NMR (400 MHz, DMSO-d₆) d 13.00 (s, 1H), 12.17 (s, 1H), 8.82 (d, J =4.4 Hz, 1H), 8.24 (d, J = 8.0 Hz, 1H), 8.16-8.12 (m, 2H), 7.93 (d, J =8.8 Hz, 1H), 7.76 (dd, J = 7.2, 4.8 Hz, 1H), 7.64 (s, 1H), 7.52 (dd, J =8.4, 1.6 Hz, 1H), 7.47 (d, J = 8.4 Hz, 1H), 7.32 (d, J = 8.4 Hz, 1H),2.32 (s, 3H); LCMS (electrospray) m/z 386.1 (M + H)+. AN-(6-(5-methyl-1H-indazol-4- yl)benzo[d]thiazol-2-yl)picolinamide 13

¹H NMR (400 MHz, DMSO-d₆) δ 13.31(s, 1H), 12.74(brs, 1H), 8.43(s, 1H),7.93(d, J = 1.6 Hz, 1H), 7.73(d, J = 2.4 Hz, 1H), 7.71(s, 1H), 7.60(d, J= 3.2 Hz, 2H), 7.36-7.34(m, 1H), 7.31(dd, J = 8.4 Hz, J = 1.2 Hz, 1H),6.92-6.89(m, 1H), 6.86-6.85(m, 1H), 2.03-1.98(m, 1H), 0.99-0.95(m, 4H);LCMS (electrospray) m/z 417.0 (M + H)+. BN-(6-(5-(thiophen-2-yl)-1H-indazol-4- yl)benzo[d]thiazol-2-yl)cyclopropanecarboxamide 14

¹H NMR (400 MHz, DMSO-d₆) δ 13.07(s, 1H), 12.62(s, 1H), 8.25(s, 1H),8.08(s, 1H), 8.03(s, 1H), 7.77-7.67(m, 3H), 7.59(d, J = 8.0 Hz, 1H),2.00- 1.96(m, 1H), 0.96-0.92(m, 4H); LCMS (electrospray) m/z 335.1 (M +H)+. A N-(6-(1H-indazol-4-yl)benzo[d]thiazol-2-yl)cyclopropanecarboxamide 15

¹H NMR (400 MHz, DMSO-d₆) δ 13.27(s, 1H), 12.69(s, 1H), 8.21(s, 1H),8.00(s, 1H), 7.84(d, J = 8.4 Hz, 1H), 7.65(dd, J = 8.4 Hz, J = 1.6 Hz,1H), 7.54(dd, J = 10.8 Hz, J = 9.2 Hz, 1H), 2.02-1.96(m 1H),0.95-0.93(m, 4H); LCMS (electrospray) m/z 353.1 (M + H)+. BN-(6-(5-fluoro-1H-indazol-4- yl)benzo[d]thiazol-2-yl)cyclopropanecarboxamide 16

¹H NMR (400 MHz, DMSO-d₆) δ 13.38(s, 1H), 12.74(s, 1H), 8.09(d, J = 1.6Hz, 1H), 7.83(d, J = 8.8 Hz, 1H), 7.72(s, 1H), 7.55(d, J = 8.8 Hz, 1H),7.51(dd, J = 8.4 Hz, J = 1.6 Hz, 1H), 7.46(d, J = 8.8 Hz, 1H),2.02-1.97(m, 1H), 0.97-0.93(m, 4H); LCMS (electrospray) m/z 369.0 (M +H)+. B N-(6-(5-chloro-1H-indazol-4- yl)benzo[d]thiazol-2-yl)cyclopropanecarboxamide 17

¹H NMR (400 MHz, DMSO-d₆) δ 13.58(s, 1H), 12.74(s, 1H), 8.03(d, J = 1.6Hz, 1H), 7.84(d, J = 8.0 Hz, 1H), 7.75(s, 2H), 7.71(s, 1H), 7.44(dd, J =8.8 Hz, 1.6 Hz, 1H), 20.4-2.00(m, 1H), 0.99-0.96(m, 4H); LCMS(electrospray) m/z 403.0 (M + H)+. BN-(6-(5-(trifluoromethyl)-1H-indazol-4- yl)benzo[d]thiazol-2-yl)cyclopropanecarboxamide 18

¹H NMR (400 MHz, DMSO-d₆) δ 13.19(s, 1H), 12.64(s, 1H), 7.84(s, 1H),7.75(s, 1H), 7.65(d, J = 8.0 Hz, 1H), 7.55(d, J = 8.0 Hz, 1H), 7.48(d, J= 8.0 Hz, 1H), 7.29-7.20(m, 3H), 6.63(d, J = 4.0 Hz, 1H), 3.66-3.62(m,1H), 2.01-1.92(m, 1H), 0.98-0.85(m, 4H); LCMS (electrospray) m/z 417.1(M + H)+. B N-(6-(5-(thiophen-3-yl)-1H-indazol-4- yl)benzo[d]thiazol-2-yl)cyclopropanecarboxamide 19

¹H NMR (400 MHz, DMSO-d₆) δ 13.75(s, 1H), 12.71(s, 1H), 8.35(s, 2H),7.86(d, J = 6.8 Hz, 1H), 7.79(s, 1H), 7.53(d, J = 6.8 Hz, 1H), 7.28(d, J= 6.0 Hz, 1H), 2.05-1.95(m, 1H), 1.10-0.90(m, 4H); LCMS (electrospray)m/z 369.0 (M + H)+. B N-(6-(7-chloro-1H-indazol-4- yl)benzo[d]thiazol-2-yl)cyclopropanecarboxamide 20

¹H NMR (400 MHz, DMSO-d₆) δ 13.36(s, 1H), 12.73(s, 1H), 8.39(s, 1H),8.27(s, 1H), 7.88- 7.81(m, 2H), 7.62(s, 1H), 7.31(s, 1H), 2.04- 1.99(m,1H), 0.99-0.97(m, 4H); LCMS (electrospray) m/z 369.0 (M + H)+. BN-(6-(6-chloro-1H-indazol-4- yl)benzo[d]thiazol-2-yl)cyclopropanecarboxamide 21

¹H NMR (400 MHz, DMSO-d₆) δ 13.42 (s, NH), 12.70(s, NH), 7.95 (s, 1H),7.84-7.82 (m, 2H), 7.75 (d, J = 8.4 Hz, 1H), 7.60(d, J = 9.6 Hz, 1H),7.44(d, J = 10.0 Hz, 1H), 2.02-1.98(m, 1H), 1.08 (s, 9 H), 0.98-0.96 (m,4H); LCMS (electrospray) m/z 435.1 (M + H)+. B tert-butyl 4-(2-(cyclopropanecarboxamido)benzo[d]thiazol-6-yl)-1H-indazole-5-carboxylate 22

¹H NMR (400 MHz, DMSO-d₆) δ 13.28(s, 1H), 12.74(s, 1H), 8.43(s, 1H),8.23(s, 1H), 7.88- 7.87(m, 2H), 7.72-7.71(m, 2H), 7.61-7.59(m, 2H),7.19(dd, J = 5.2 Hz, J = 3.2 Hz, 1H), 2.07-2.00(m, 1H), 1.01-0.97(m,4H); LCMS (electrospray) m/z 417.0 (M + H)+. BN-(6-(6-(thiophen-2-yl)-1H-indazol-4- yl)benzo[d]thiazol-2-yl)cyclopropanecarboxamide 23

¹H NMR (400 MHz, DMSO-d₆) δ 13.31 (s, NH), 12.71 (s, NH), 8.45-8.42 (m,1H), 8.02 (s, 1H), 7.90 (s, 1H), 7.72-7.70 (d, J = 8.0 Hz, 1H), 7.48-7.50 (d, J = 8.4 Hz, 1H), 7.46 (m, 4H), 6.76 (m, 1H), 4.24 (d, J = 5.2Hz, 1H), 2.03-2.01 (m, 1H), 0.99-0.97 (m, 4H); LCMS (electrospray) m/z474.1 (M + H)+. B 4-(2- (cyclopropanecarboxamido)benzo[d]thiazol-6-yl)-N-(thiophen-3-ylmethyl)-1H- indazole-5-carboxamide 24

¹H NMR (400 MHz, DMSO-d₆) δ 13.03(s, 1H), 12.67(s, 1H), 8.11(d, J = 3.2Hz, 1H), 7.82-7.80(m, 2H), 7.60(dd, J = 8.4 Hz, J = 1.6 Hz, 1H), 7.53(d,J = 9.2 Hz, 1H), 7.34(d, J = 8.4 Hz, 1H), 3.75(s, 3H), 2.05-1.98(m, 1H),0.98-0.96(m, 4H); LCMS (electrospray) m/z 365.1 (M + H)+. BN-(6-(5-methoxy-1H-indazol-4- yl)benzo[d]thiazol-2-yl)cyclopropanecarboxamide 25

¹H NMR (400 MHz, DMSO-d₆) δ 13.13(s, 1H), 12.72(s, 1H), 8.07(d, J = 1.6Hz, 1H), 7.84(d, J = 8.0 Hz, 1H), 7.71(s, 1H), 7.58-7.53(m, 3H), 5.15-5.08(m, 1H), 4.45(d, J = 5.2 Hz, 2H), 2.04-1.99(m, 1H), 1.02-0.96(m,4H); LCMS (electrospray) m/z 365.0 (M + H)+. BN-(6-(5-(hydroxymethyl)-1H-indazol-4- yl)benzo[d]thiazol-2-yl)cyclopropanecarboxamide 26

¹H NMR (400 MHz, DMSO-d₆) δ 13.03 (s, NH), 12.77 (s, NH), 7.97 (s, 1H),7.86 (d, J = 8.4 Hz, 1H), 7.49-7.38 (m, 3H), 4.20 (br, NH2), 2.10 (m,1H), 1.99 (s, 3H), 0.99-0.96 (m, 4H); LCMS (electrospray) m/z 364.1 (M +H)+. B N-(6-(3-amino-5-methyl-1H-indazol-4- yl)benzo[d]thiazol-2-yl)cyclopropanecarboxamide. 3 HCl 27

¹H NMR (400 MHz, DMSO-d₆) δ 12.85 (s, 1H), 12.61 (s, 1H), 9.02 (s, 1H),8.11 (s, 1H), 7.77-7.75 (m, 2H), 7.65 (d, J = 9.2 Hz, 1H), 7.34 (d, J =8.6 Hz, 1H), 7.07 (d, J = 8.6 Hz, 1H), 1.97 (quin, J = 6.2 Hz, 1H), 0.94(d, J = 6.0 Hz, 4H); LCMS (electrospray) m/z 351.40 (M + H)+. BN-(6-(5-hydroxy-1H-indazol-4- yl)benzo[d]thiazol-2-yl)cyclopropanecarboxamide 28

¹H NMR (400 MHz, DMSO-d₆) δ 13.04(s, 1H), 12.69(s, 1H), 7.99(d, J = 1.2Hz, 1H), 7.84(d, J = 8.4 Hz, 1H), 7.55(s, 1H), 7.50(d, J = 8.4 Hz, 1H),7.42(dd, J = 7.6 Hz, 1.6 Hz, 1H), 7.35(d, J = 9.2 Hz, 1H), 2.0(q, J =7.6 Hz, 2H), 2.05-1.99(m, 1H), 1.08(t, J = 7.6 Hz, 3H), 0.98-0.96(m,4H); LCMS (electrospray) m/z 363.1 (M + H)+. BN-(6-(5-ethyl-1H-indazol-4- yl)benzo[d]thiazol-2-yl)cyclopropanecarboxamide 29

¹H NMR (400 MHz, DMSO-d₆) δ 13.68(s, 1H), 12.76(s, 1H), 8.28(d, J = 1.6Hz, 1H), 8.07(s, 1H), 7.89(d, J = 8.4 Hz, 1H), 7.75(d, J = 9.2 Hz, 1H),7.69(dd, J = 8.4 Hz, J = 1.6 Hz, 2H), 2.03-1.96(m, 1H), 0.96-0.94(m,4H); LCMS: m/z = 403.0 (M + H+)LCMS (electrospray) m/z 360.1 (M + H)+. BN-(6-(5-cyano-1H-indazol-4- yl)benzo[d]thiazol-2-yl)cyclopropanecarboxamide 30

¹H NMR (400 MHz, DMSO-d₆) 13.37(s, 1H), 12.76(s, 1H), 8.15(d, J = 1.6Hz, 1H), 7.88(d, J = 8.4 Hz, 1H), 7.77(brs, 1H), 7.60-7.55(m, 2H),7.50(d, J = 9.2 Hz, 1H), 5.16-4.95(m, 1H), 2.28-2.21(m, 1H),1.81-1.71(m, 1H), 1.38-1.28(m, 1H); LCMS (electrospray) m/z 387.0 (M +H)+. B (1S,2S)-N-(6-(5-chloro-1H-indazol-4- yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 31

¹H NMR (400 MHz, DMSO-d₆) 12.85(s, 1H), 12.76(s, 1H), 8.19 (s, 1H),7.81-7.78 (m, 2H), 7.68 (d, J = 9.2 Hz, 1H), 7.56 (d, J = 8.6 Hz, 1H),7.34 (d, J = 8.6 Hz, 1H), 5.16-4.95 (m, 1H), 4.26 (t, J = 4.4 Hz, 2H),3.32 (t, J = 4.4 Hz, 2H), 2.45 (s, 6H), 2.28- 2.21(m, 1H), 1.78-1.68 (m,1H), 1.38-1.28(m, 1H); LCMS (electrospray) m/z 440.10 (M + H)+. B(1S,2S)-N-(6-(5-(2- (dimethylamino)ethoxy)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide. 3 HCl 32

¹H NMR (400 MHz, DMSO-d₆) δ 14.14 (s, NH), 13.08 (s, NH), 8.12 (s, 1H),7.94-7.92 (m, 1H), 7.65 (s, 1H), 7.55 (dd, J12 = 1.6 Hz, J13 = 8.4 Hz,1H), 7.47 (d, J = 8.4 Hz, 1H), 7.32 (d, J = 8.8 Hz, 1H), 2.75 (m, 1H),2.31 (s, 3H), 1.21-1.17 (m, 4H); LCMS (electrospray) m/z 365.0 (M + H)+.A N-(6-(5-methyl-1H-indazol-4- yl)benzo[d]thiazol-2-yl)cyclopropanecarbothioamide 33

¹H NMR (400 MHz, DMSO-d₆) δ 13.50(s, 1H), 12.85(s, 1H), 8.11(s, 1H),7.91(d, J = 8.4 Hz, 2H), 7.85(s, 1H), 7.72(d, J = 4.0 Hz, 2H), 7.50(d, J= 8.8 Hz, 1H), 6.82(t, J = 55.2 Hz, 1H), 5.14-4.98(m, 1H), 2.25-2.22(m,1H), 1.82-1.72(m, 1H), 1.37-1.30(m, 1H); 19F NMR (400 MHz, DMSO-d6) δ−102.50(d, J = 56.8 Hz, 1H), −103.08(d, J = 56.8 Hz, 1H),219.66-219.92(m, 1H); LCMS (electrospray) m/z = 403.0 (M + H+) B(1S,2S)-N-(6-(5-(difluoromethyl)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide34

¹H NMR (400 MHz, DMSO-d₆) 12.85(s, 1H), 12.77(s, 1H), 8.21 (s, 1H), 7.86(s, 1H), 7.83 (d, J = 8.4 Hz, 1H), 7.68 (d, J = 8.4 Hz, 1H), 7.52 (d, J= 9.2 Hz, 1H), 7.32 (d, J = 9.2 Hz, 1H), 5.13-4.96 (m, 1H), 4.08 (t, J =4.6 Hz, 2H), 3.53 (t, J = 4.4 Hz, 2H), 3.21 (s, 3H), 2.29-2.22(m, 1H),1.80-1.70 (m, 1H), 1.36-1.27(m, 1H); LCMS (electrospray) m/z 427.10 (M +H)+. B (1S,2S)-2-fluoro-N-(6-(5-(2- methoxyethoxy)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)cyclopropane-1- carboxamide. 2 HCl 35

¹H NMR (400 MHz, DMSO-d₆) δ 13.22(s, 1H), 12.78(s, 1H), 8.02(d, J = 1.6Hz, 1H), 7.86(d, J = 8.0 Hz, 1H), 7.77(d, J = 8.8 Hz, 1H), 7.70(s, 1H),7.55(d, J = 8.8 Hz, 1H), 7.43(dd, J = 8.4 Hz, J = 2.0 Hz, 1H), 6.69(dd,J = 17.6 Hz, J = 10.8 Hz, 1H), 5.76(d, J = 16.4 Hz, 1H), 5.16(d, J =12.0 hz, 1H), 5.13-4.94(m, 1H), 2.24-2.20(m, 1H), 1.72-1.71(m, 1H),1.35-1.28(m, 1H); LCMS (electrospray) m/z = 379.1 (M + H+) B(1S,2S)-2-fluoro-N-(6-(5-vinyl-1H- indazol-4-yl)benzo[d]thiazol-2-yl)cyclopropane-1-carboxamide 36

¹H NMR (400 MHz, DMSO-d₆) δ 12.77(s, 1H), 8.13(dd, J = 4.4 Hz, 1.6 Hz,1H), 7.92(dd, J = 8.4 Hz, 6.4 Hz, 1H), 7.88(d, J = 7.6 Hz, 1H),7.64-7.54(m, 3H), 5.10-4.92(m, 1H), 5.39-5.27(m, 1H), 4.73- 4.60(m, 1H),2.22-2.21(m, 1H), 1.69-1.68(m, 1H), 1.30-1.25(m, 1H); LCMS(electrospray) m/z = 383.1. (M + H+) B(1S,2S)-2-fluoro-N-(6-(5-(fluoromethyl)-1H-indazol-4-yl)benzo[d]thiazol-2- yl)cyclopropane-1-carboxamide. 2 HCl37

¹H NMR (400 MHz, DMSO-d₆) δ 13.01(s, 1H), 12.74(s, 1H), 8.07(s, 1H),7.83(dd, J = 8.4 Hz, 1H), 7.58(s, 1H), 7.51(d, J = 8.0 Hz, 1H), 7.41(d,J = 8.8 Hz, 1H), 6.95(dd, J = 8.4 Hz, 1.2 Hz, 1H), 5.10- 4.92(m, 1H),2.21-2.17(m, 1H), 1.94-1.90(m, 1H), 1.74-1.69(m, 1H), 1.30-1.11(m, 1H),0.82-0.75(m, 1H), 0.60-0.59(m, 1H); LCMS (electrospray) m/z = 393.1 (M +H+) B (1S,2S)-N-(6-(5-cyclopropyl-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide 38

¹H NMR (400 MHz, DMSO-d₆) δ 12.79(s, 1H), 8.06(d, J = 2.0 Hz, 1H),7.84(d, J = 8.0 Hz, 1H), 7.67(s, 1H), 7.55-7.53(m, 2H), 7.48(d, J = 8.8Hz, 1H), 7.39(d, J = 1.2 Hz, 1H), 7.16(d, J = 8.8 Hz, 1H), 6.18-6.17(m,1H), 5.29(s, 2H), 5.10-4.93(m, 1H), 2.23-2.20(m, 1H), 1.76-1.68(m, 1H),1.31-1.27(m, 1H); LCMS (electrospray) m/z = 433.1 (M + H+) B(1S,2S)-N-(6-(5-((1H-pyrazol-1- yl)methyl)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide 39

¹H NMR (400 MHz, DMSO-d₆) δ 13.35(s, 1H), 12.77(s, 1H), 8.20(d, J = 2.0Hz, 1H), 7.87(s, 1H), 7.83(d, J = 8.4 Hz, 1H), 7.66(dd, J = 8.4 Hz, 1.6Hz, 1H), 7.51(d, J = 3.2 Hz, 1H), 5.12-4.91(m, 1H), 3.91(s, 1H),2.21-2.18(m, 1H), 1.75-1.68(m, 1H), 1.29-1.23(m, 1H); LCMS(electrospray) m/z = 377.1 (M + H+) B(1S,2S)-N-(6-(5-ethynyl-1H-indazol-4- yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 40

¹H NMR (400 MHz, DMSO-d₆) δ 13.15 (s, NH), 12.80 (s, NH), 8.09 (s, 1H),7.88 (d, J = 8.0 Hz, 1H), 7.67 (s, 1H), 7.50 (d, J = 8.0 Hz, 1H), 7.35(d, J = 9.6 Hz, 1H), 4.96-5.15 (m, 1H), 2.25-2.22 (m, 1H), 2.18 (s, 3H),1.79-1.72 (m, 1H), 1.33-1.31 (m, 1H); LCMS (electrospray) m/z 385.1 (M +H)+. B (1S,2S)-2-fluoro-N-(6-(6-fluoro-5-methyl-1H-indazol-4-yl)benzo[d]thiazol-2- yl)cyclopropane-1-carboxamide 41

¹H NMR (400 MHz, DMSO-d₆) δ 13.15 (s, NH), 12.80 (s, NH), 8.09 (s, 1H),7.88 (d, J = 8.0 Hz, 1H), 7.67 (s, 1H), 7.50 (d, J = 8.0 Hz, 1H), 7.35(d, J = 9.6 Hz, 1H), 4.96-5.15 (m, 1H), 2.25-2.22 (m, 1H), 2.18 (s, 3H),1.79-1.72 (m, 1H), 1.33-1.31 (m, 1H); LCMS (electrospray) m/z 385.1 (M +H)+. B (1S,2S)-N-(6-(5-chloro-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide42

¹H NMR (400 MHz, DMSO-d₆) δ 13.46 (s, NH), 12.83 (s, NH), 8.19 (s, 1H),7.90 (d, J = 8.4 Hz, 1H), 7.80 (s, 1H), 7.64 (d, J = 8.8 Hz, 1H), 5.16-4.95 (m, 1H), 2.28-2.21 (m, 1H), 1.79-1.72 (m, 1H), 1.35-1.28 (m, 1H);LCMS (electrospray) m/z = 405.0 (M + H+) B(1S,2S)-N-(6-(5-bromo-6-fluoro-1H- indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 43

¹H NMR (400 MHz, DMSO-d₆) δ 13.59 (s, NH), 12.79 (s, NH), 8.05 (s, 1H),7.87 (d, J = 8.0 Hz, 1H), 7.71 s, 1H), 7.46-7.40 (m, 2H), 6.48 (dd, J12= 11.8 Hz, J13 = 17.8 Hz, 1H), 5.35 (dd, J12 = 2.6 Hz, J13 = 14.2 Hz,1H), 5.16-4.95 (m, 1H), 2.26-2.21 (m, 1H), 1.79-1.72 (m, 1H), 1.35-1.29(m, 1H); LCMS (electrospray) m/z 449.0 (M + H)+. B(1S,2S)-2-fluoro-N-(6-(6-fluoro-5-vinyl-1H-indazol-4-yl)benzo[d]thiazol-2- yl)cyclopropane-1-carboxamide 44

¹H NMR (400 MHz, DMSO-d₆) δ 13.34 (s, 1H), 12.77 (d, J = 3.2 Hz, 1H),7.88 (d, J = 1.6 Hz, 1H), 7.80 (d, J = 8.4 Hz, 1H), 7.38 (d, J = 9.6 Hz,1H), 7.30 (dd, J = 2.0, 6.4 Hz, 1H), 5.10 (m, 0.5H), 4.93 (m, 0.5H),2.20 (m, 1H), 2.00 (m, 3H), 1.71 (m, 1H), 1.28 (m, 1H), LCMS(electrospray) m/z 419.05 (M + H)+. B(1S,2S)-N-(6-(3-chloro-6-fluoro-5-methyl-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 45

¹H NMR (400 MHz, DMSO-d₆) δ 13.55 (s, 1H), 12.79 (d, J = 3.6 Hz, 1H),7.87 (d, J = 2.0 Hz, 1H), 7.86 (d, J = 7.6 Hz, 1H), 7.41 (d, J = 10.0Hz, 1H), 7.28 (dd, J = 1.6 Hz, 1H), 5.14 (m, 0.5H), 4.97 (m, 0.5H), 2.23(m, 1H), 2.00 (m, 3H), 1.76 (m, 1H), 1.31 (m, 1H), LCMS (electrospray)m/z 511.00 (M + H)+. B (1S,2S)-2-fluoro-N-(6-(6-fluoro-3-iodo-5-methyl-1H-indazol-4-yl)benzo[d]thiazol- 2-yl)cyclopropane-1-carboxamide46

¹H NMR (400 MHz, DMSO-d₆) δ 13.15 (s, NH), 12.80 (s, NH), 8.04 (s, 1H),7.87 (d, J = 8.0 Hz, 1H), 7.56 (s, 1H), 7.44 (d, J = 8.4 Hz, 1H),5.15-4.96 (m, 1H), 2.58-2.54 (m, 2H), 2.25-2.22 (m, 1H), 1.78- 1.72 (m,1H), 1.33-1.30 (m, 1H), 1.06 (t, 3H); LCMS (electrospray) m/z 399.1 (M +H)+. B (1S,2S)-N-(6-(5-ethyl-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide47

¹H NMR (400 MHz, DMSO-d₆) δ 13.41(s, 1H), 12.78(s, 1H), 8.23(d, J = 1.6Hz, 1H), 7.89(s, 1H), 7.84(d, J = 8.4 Hz, 1H), 7.67(d, J = 8.4 Hz, 1H),7.46(d, J = 9.6 Hz, 1H), 5.11-4.92(m, 1H), 4.19(s, 1H), 2.21-2.18(m,1H), 1.77-1.67(m, 1H), 1.33- 1.25(m, 1H); LCMS (electrospray) m/z 395.1(M + H+) B (1S,2S)-N-(6-(5-ethynyl-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide48

¹H NMR (400 MHz, DMSO-d₆) δ 13.34(s, 1H), 12.77(s, 1H), 8.01(d, J = 2.0Hz, 1H), 7.84(d, J = 8.4 Hz, 1H), 7.60(s, 1H), 7.45(d, J = 8.4 Hz, 1H),7.41(dd, J = 8.4 Hz, J = 1.2 Hz, 1H), 5.12-4.92(m, 1H), 2.21-2.19(m,1H), 1.76-1.69(m, 1H), 1.31- 1.26(m, 1H); LCMS (electrospray) m/z 497.0(M + H+) B (1S,2S)-2-fluoro-N-(6-(6-fluoro-5-iodo-1H-indazol-4-yl)benzo[d]thiazol-2- yl)cyclopropane-1-carboxamide 49

¹H NMR (400 MHz, DMSO-d₆) δ 13.49 (s, 1H), 12.78 (d, J = 3.6 Hz, 1H),7.89 (d, J = 1.6 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.43 (d, J = 10 Hz,1H), 7.31 (dd, J = 1.6, 6.8 Hz, 1H), 5.14 (m, 0.5H), 4.95 (m, 0.5H),2.24 (m, 1H), 2.02 (t, J = 2.4 Hz, 3H), 1.75 (m, 1H), 1.31 (m, 1H); LCMS(electrospray) m/z 464.00 (M + H)+. B(1S,2S)-N-(6-(3-bromo-6-fluoro-5-methyl-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 50

¹H NMR (400 MHz, DMSO-d₆) δ 13.67(s, 1H), 12.82(s, 1H), 8.03(s, 1H),7.82(d, J = 8.4 Hz, 1H), 7.66-7.64(m, 1H), 7.41(d, J = 8.4 Hz, 1H),5.15- 4.95(m, 1H), 2.26-2.23(m, 1H), 1.79-1.72(m, 1H), 1.34-1.28(m, 1H);LCMS (electrospray) LCMS: m/z 439.1 (M + H+) B(1S,2S)-2-fluoro-N-(6-(6-fluoro-5- (trifluoromethyl)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)cyclopropane-1- carboxamide 51

¹H NMR (400 MHz, DMSO-d₆) δ 13.75 (s, 1H), 12.82 (s, 1H), 8.09 (d, J =1.6 Hz, 1H), 7.88 (d, J = 8.4 Hz, 1H), 7.79 (brs, 1H), 7.50 (dd, J =1.6, 6.4 Hz, 1H), 5.14 (m, 0.5H), 4.97 (m, 0.5H), 2.23 (m, 4H), 1.76 (m,1H), 1.32 (m, 1H); LCMS (electrospray) m/z 419.00 (M + H)+. B(1S,2S)-N-(6-(7-chloro-6-fluoro-5-methyl-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 52

¹H NMR (400 MHz, DMSO-d₆) δ 13.16 (s, 1H), 12.81 (s, 1H), 7.91 (d, J =1.6 Hz, 1H), 7.87 (d, J = 8.4 Hz, 1H), 7.33 (m, 2H), 5.73 (m, 1H), 5.59(m, 1H), 5.14 (m, 0.5H), 4.97 (m, 0.5H), 4.84 (m, 1H), 2.25 (m, 1H),2.01 (t, J = 2.4 Hz, 3H) 1.76 (m, 1H), 1.32 (m, 1H); LCMS (electrospray)m/z 411.10 (M + H)+. B (1S,2S)-2-fluoro-N-(6-(6-fluoro-5-methyl-3-vinyl-1H-indazol-4-yl)benzo[d]thiazol- 2-yl)cyclopropane-1-carboxamide53

¹H NMR (400 MHz, DMSO-d₆) δ 14.00(s, 1H), 12.80(s, 1H), 7.92(d, J = 1.2Hz, 1H), 7.84(d, J = 8.4 Hz, 1H), 7.34(dd, J = 8.4 Hz, J = 1.6 Hz, 1H),5.15- 4.97(m, 1H), 2.26-2.24(m, 1H), 2.08(s, 3H), 1.79- 1.76(m, 1H),1.32-1.27(m, 1H); LCMS (electrospray) m/z 454.0 (M + H+) B(1S,2S)-N-(6-(3,7-dichloro-6-fluoro-5-methyl-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 54

¹H NMR (400 MHz, DMSO-d₆) δ 14.03(s, 1H), 13.21(s, 1H), 7.94(d, J = 1.6Hz, 1H), 7.50(d, J = 1.6 Hz, 1H), 5.14-4.95(m, 1H), 2.25-2.22(m, 1H),2.09(s, 3H), 1.80-1.70(m, 1H), 1.36-1.29(m, 1H); LCMS (electrospray) m/z487.0 (M + H+) B (1S,2S)-N-(4-chloro-6-(3,7-dichloro-6-fluoro-5-methyl-1H-indazol-4- yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 55

¹H NMR (400 MHz, DMSO-d₆) δ 13.33(s, 1H), 12.80(s, 1H), 8.06(s, 1H),7.84(d, J = 8.0 Hz, 1H), 7.43-7.41(m, 1H), 5.13-4.97(m, 1H),2.23-2.20(m, 1H), 2.16(s, 3H), 1.77-1.72(m, 1H), 1.44-1.41(m, 1H); LCMS(electrospray): m/z 421.0 (M + H+) B(1S,2S)-2-fluoro-N-(6-(3,6,7-trifluoro-5-methyl-1H-indazol-4-yl)benzo[d]thiazol- 2-yl)cyclopropane-1-carboxamide56

¹H NMR (400 MHz, DMSO-d₆) δ 12.78 (s, 1H), 12.60 (s, 1H), 8.09 (s, 1H),8.06 (s, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.43-7.41 (m, 1H), 5.13-4.97 (m,1H), 2.23-2.20 (m, 1H), 2.16 (s, 3H), 1.77-1.72 (m, 1H), 1.44-1.41 (m,1H); LCMS (electrospray): m/z 403.0 (M + H)+. B(1S,2S)-N-(6-(6,7-difluoro-5-methyl-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide57

¹H NMR (400 MHz, DMSO-d₆) δ 13.59 (s, 1H), 12.81 (s, 1H), 8.15 (s, 1H),7.88 (d, J = 8.0 Hz, 1H), 7.82 (s, 1H), 7.34 (dd, J = 8.4 Hz, J = 1.6Hz, 1H), 5.18-5.12 (m, 0.5H), 5.01-4.96 (m, 0.5H), 2.50 (t, J = 1.6 Hz,3H), 2.29-2.21 (m, 1H), 1.85-1.72 (m, 1H), 1.38-1.29 (m, 1H); LCMS(electrospray) m/z 419.0 (M + H)+. B(1S,2S)-N-(6-(5-chloro-6-fluoro-7-methyl-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 58

¹H NMR (400 MHz, DMSO-d₆) δ 13.76 (br s, 1H), 12.82 (br s, 1H), 8.19 (d,J = 1.7 Hz, 1H), 7.96-7.82 (m, 2H), 7.59 (dd, J = 1.8, 8.4 Hz, 1H),5.26-4.85 (m, 1H), 2.57 (s, 3H), 2.30-2.19 (m, 1H), 1.84- 1.69 (m, 1H),1.33 (tdd, J = 6.4, 9.0, 12.9 Hz, 1H); LCMS (electrospray) m/z 450.8(M + H)+. B (1S,2S)-N-(6-(5-chloro-6-fluoro-7-(methylthio)-1H-indazol-4- yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 59

¹H NMR (400 MHz, DMSO-d₆) δ 13.36 (s, 1H), 12.77 (br s, 1H), 8.04 (s,1H), 7.87 (dd, J12 = 4.8 Hz, J13 = 8.4 Hz, 1H), 7.66 (s, 1H), 7.45 (d, J= 7,6 Hz, 1H), 5.14-4.95 (m, 1H), 2.49 (d, J = 1.7 Hz, 3H), 2.21 (d, J =2.8 Hz, 3H), 2.18-2.10 (m, 1H), 1.75-1.61 (m, 1H), 1.27-1.10 (m, 1H);LCMS (electrospray) m/z 399.1 (M + H)+. B(1S,2S)-2-fluoro-N-(6-(6-fluoro-5,7-dimethyl-1H-indazol-4-yl)benzo[d]thiazol-2-yl)cyclopropane-1-carboxamide. 2 TFA 60

¹H NMR (400 MHz, DMSO-d₆) δ 12.87 (s, 1H), 12.85 (s, 1H), 8.22 (s, 1H),7.88 (m, 2H), 7.60 (dd, J12 = 1.8 Hz, J13 = 8.2 Hz, 1H), 5.13-4.97 (m,1H), 2.28-2.21 (m, 1H), 1.95 (s, 3H), 1.92 (s, 3H), 1.81- 1.71 (m, 1H),1.37-1.28 (m, 1H); LCMS (electrospray) m/z 481.1 (M + H)+. B(1S,2S)-N-(6-(5-chloro-7- (dimethylphosphoryl)-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide61

¹H NMR (400 MHz, DMSO-d₆) δ 13.70 (s, 1H), 12.82 (s, 1H), 8.19 (d, J =2.0 Hz, 1H), 7.90 (d, J = 8.4 Hz, 2H), 7.59 (dd, J = 6.8 Hz, J = 2.0 Hz,1H), 7.10 (q, J = 12.4 Hz, 1H), 6.22 (brs, 1H), 5.81 (d, J = 11.6 Hz,1H), 5.16-5.12 (m, 0.5H), 4.99-4.96 (m, 0.5H), 2.28-2.21 (m, 1H),1.81-1.71 (m, 1H), 1.37-1.28 (m, 1H); LCMS (electrospray) m/z 431.0 (M +H)+. B (1S,2S)-N-(6-(5-chloro-6-fluoro-7-vinyl-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 62

¹H NMR (400 MHz, DMSO-d₆) δ 13.37 (s, 1H), 12.79 (s, 1H), 8.08 (s, 1H),7.88 (d, J = 8.4 Hz, 1H), 7.49 (d, J = 8.0 Hz, 1H), 7.11-7.09 (m, 1H),6.16 (d, J = 18.4 Hz, 1H), 5.70 (d, J = 12.0 Hz, 1H), 5.14-4.97 (m, 1H),2.28-2.21 (m, 1H), 2.20 (s, 3H), 1.81-1.71 (m, 1H), 1.37-1.28 (m, 1H);LCMS (electrospray) m/z 411.1 (M + H)+. B(1S,2S)-2-fluoro-N-(6-(6-fluoro-5-methyl-7-vinyl-1H-indazol-4-yl)benzo[d]thiazol- 2-yl)cyclopropane-1-carboxamide63

¹H NMR (400 MHz, DMSO-d₆) δ 12.85 (s, 1H), 8.22 (s, 1H), 7.96-7.89 (m,2H), 7.49 (d, J = 8.0 Hz, 1H), 7.11-7.09 (m, 1H), 7.60 (d, J = 8.0 Hz,1H), 5.14-4.97 (m, 1H), 3.19 (s, 3H), 2.28-2.21 (m, 1H), 1.79-1.73 (m,1H), 1.37-1.28 (m, 1H); LCMS (electrospray) m/z 467.0 (M + H)+. B(1S,2S)-N-(6-(5-chloro-6-fluoro-7- (methylsulfinyl)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide. 2 HCl salt64

¹H NMR (400 MHz, DMSO-d₆) δ 12.79 (br s, 1H), 8.08 (s, 1H), 7.87 (d, J =8.0 Hz, 1H), 7.73 (s, 1H), 7.49 (d, J = 9.6 Hz, 1H), 5.14-4.96 (m, 1H),3.17 (s, 3H), 2.54 (s, 3H), 2.16 (td, J = 6.9, 13.8 Hz, 1H), 1.74-1.60(m, 1H), 1.25-1.11 (m, 1H); LCMS (electrospray) m/z 431.0 (M + H)+. B(1S,2S)-2-fluoro-N-(6-(6-fluoro-5-methyl- 7-(methylthio)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)cyclopropane-1- carboxamide 65

¹H NMR (400 MHz, METHANOL-d₄) δ 8.44- 8.32 (m, 2H), 7.84-7.76 (m, 1H),7.42-7.25 (m, 5H), 5.07-5.01 (m, 1H), 3.27-2.97 (m, 5H), 2.24- 2.15 (m,1H), 2.06 (br d, J = 2.2 Hz, 3H), 1.96- 1.81 (m, 1H), 1.38-1.28 (m, 1H);LCMS (electrospray) m/z 490.2 (M + H)+. B(1S,2S)-2-fluoro-N-(6-(6-fluoro-5-methyl-1H-indazol-4-yl)-7-(2-(pyridin-4- yl)ethyl)benzo[d]thiazol-2-yl)cyclopropane-1-carboxamide. 3 TFA 66

¹H NMR (400 MHz, DMSO-d₆) δ 13.36 (br s, 1H), 12.81 (s, 1H), 8.12 (s,1H), 7.90 (d, J = 8.4 Hz, 1H), 7.51 (d, J = 8.4 Hz, 1H), 5.14-4.96 (m,1H), 3.13 (s, 3H), 2.32 (s, 3H), 2.16 (td, J = 6.9, 13.8 Hz, 1H),1.74-1.60 (m, 1H), 1.25-1.11 (m, 1H); LCMS (electrospray) m/z 447.1 (M +H)+. B (1S,2S)-2-fluoro-N-(6-(6-fluoro-5-methyl-7-(methylsulfinyl)-1H-indazol-4- yl)benzo[d]thiazol-2-yl)cyclopropane-1-carboxamide. 2 HCl 67

¹H NMR (400 MHz, DMSO-d₆) δ 13.35 (s, 1H), 12.79 (s, 1H), 8.08 (s, 1H),7.87 (d, J = 8.4 Hz, 1H), 7.83 (br s, 1H), 7.48 (dd, J = 1.6, 6.8 Hz,1H), 5.14- 4.96 (m, 1H), 2.26-2.18 (m, 4H), 1.82-1.71 (m, 1H), 1.36-1.28(m, 1H); LCMS (electrospray) m/z 511.00 (M + H)+. B(1S,2S)-2-fluoro-N-(6-(6-fluoro-7-iodo-5-methyl-1H-indazol-4-yl)benzo[d]thiazol- 2-yl)cyclopropane-1-carboxamide68

¹H NMR (400 MHz, DMSO-d₆) δ 12.94 (s, 1H), 12.76 (s, 1H), 8.08 (d, J =1.6 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.71 (s, 1H), 7.52 (dd, J = 2.4,6.4 Hz, 1H), 5.69 (s, 2H), 5.16-4.94 (m, 1H), 2.27- 2.20 (m, 1H),1.81-1.70 (m, 1H), 1.36-1.27 (m, 1H); LCMS (electrospray) m/z 420.00(M + H)+. B (1S,2S)-N-(6-(7-amino-5-chloro-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 69

¹H NMR (400 MHz, DMSO-d₆) δ 13.47 (s, 1H), 12.79 (s, 1H), 8.13 (d, J =1.6 Hz, 1H), 7.87 (d, J = 8.4 Hz, 1H), 7.76 (s, 1H), 7.55 (dd, J = 1.6,6.8 Hz, 1H), 5.16-4.95 (m, 1H), 2.99 (s, 6H), 2.28- 2.21 (m, 1H),1.81-1.71 (m, 1H), 1.36-1.28 (m, 1H); LCMS (electrospray) m/z 448.10(M + H)+. B (1S,2S)-N-(6-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4- yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 70

¹H NMR (400 MHz, DMSO-d₆) δ 13.70 (br s, 1H), 12.81 (s, 1H), 8.15 (s,1H), 7.96 (br s, 2H), 7.90- 7.86 (m, 2H), 7.55 (d, J = 8.4 Hz, 1H),5.11-4.92 (m, 1H), 3.14 (m, 2H), 2.88 (m, 2H), 2.16 (td, J = 6.9, 13.8Hz, 1H), 1.74-1.60 (m, 1H), 1.25- 1.11 (m, 1H); LCMS (electrospray) m/z480.1 (M + H)+. B (1S,2S)-N-(6-(7-((2-aminoethyl)thio)-5-chloro-6-fluoro-1H-indazol-4- yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide. 3 HCl 71

¹H NMR (400 MHz, DMSO-d₆) δ 13.76 (s, 1H), 12.82 (s, 1H), 8.17 (d, J =0.8 Hz, 1H), 7.88 (s, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.58 (dd, J = 1.6,6.8 Hz, 1H), 5.14-4.94 (m, 1H), 3.50 (t, J = 6.0 Hz, 2H), 3.20 (s, 3H),3.17 (t, J = 6.4 Hz, 2H), 2.26-2.19 (m, 1H), 1.80-1.70 (m, 1H),1.35-1.26 (m, 1H); LCMS (electrospray) m/z 495.10 (M + H)+. B(1S,2S)-N-(6-(5-chloro-6-fluoro-7-((2- methoxyethyl)thio)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide 72

¹H NMR (400 MHz, DMSO-d₆) δ 13.29 (s, 1H), 10.42 (s, 1H), 7.80 (s, 1H),7.75 (d, J = 1.6 Hz, 1H), 7.49 (d, J = 8.4 Hz, 1H), 7.31 (dd, J = 1.6,6.8 Hz, 1H), 6.58 (q, J = 10 Hz, 1H), 6.32 (dd, J = 1.6, 15.2 HZ, 1H),5.83 (d, J = 10 Hz, 1H), 4.86-4.65 (m, 1H), 1.95 (d, J = 14 Hz, 1H),1.85 (m, 1H), 1.69- 1.55 (m, 1H), 0.95-0.87 (m, 1H); LCMS (electrospray)m/z 474.00 (M + H)+. B (1S,2S)-N-(6-(7-acrylamido-5-chloro-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 73

¹H NMR (400 MHz, DMSO-d₆) δ 13.78 (br s, 1H), 12.81 (s, 1H), 8.18 (s,1H), 7.99 (t, J = 5.2 Hz, 1H), 7.89-7.87 (m, 2H), 7.59 (d, J = 8.4 Hz,1H), 5.13- 4.96 (m, 1H), 3.29 (m, 2H), 3.00 (m, 2H), 2.16 (td, J = 6.9,13.8 Hz, 1H), 1.75 (s, 3H), 1.74-1.60 (m, 1H), 1.25-1.11 (m, 1H); LCMS(electrospray) m/z 522.1 (M + H)+. B(1S,2S)-N-(6-(7-((2-acetamidoethyl)thio)-5-chloro-6-fluoro-1H-indazol-4- yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 74

¹H NMR (400 MHz, DMSO-d₆) δ 13.50 (br s, 1H), 12.82 (s, 1H), 8.14 (s,1H), 7.88 (d, J = 8.4 Hz, 1H), 7.81 (s, 1H), 7.55 (d, J = 8.4 Hz, 1H),5.14-4.76 (m, 1H), 3.83 (m, 4H), 3.28 (m, 4H), 2.16 (td, J = 6.9, 13.8Hz, 1H), 1.74-1.60 (m, 1H), 1.25-1.11 (m, 1H); LCMS (electrospray) m/z490.1 (M + H)+. B (1S,2S)-N-(6-(5-chloro-6-fluoro-7-morpholino-1H-indazol-4- yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 HCl 75

¹H NMR (400 MHz, DMSO-d₆) δ 13.60 (s, 1H), 12.82 (s, 1H), 8.13 (s, 1H),7.88 (d, J = 8.4 Hz, 1H), 7.84 (s, 1H), 7.54 (d, J = 8.4 Hz, 1H),5.16-4.97 (m, 1H), 3.55 (br s, 6H), 3.39 (br s, 2H), 2.90 (d, J = 8.0Hz, 3H), 2.19-2.10 (m, 1H), 1.73-1.60 (m, 1H), 1.35-1.28 (m, 1H); LCMS(electrospray) m/z 503.1 (M + H)+. B(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(4-methylpiperazin-1-yl)-1H-indazol-4- yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide. 3 HCl 76

¹H NMR (400 MHz, DMSO-d₆) δ 13.56 (s, 1H), 12.82 (s, 1H), 8.71 (br s,1H), 8.13 (s, 1H), 7.89 (d, J = 8.4 Hz, 1H), 7.84 (s, 1H), 7.54 (d, J =8.4 Hz, 1H), 5.13-4.98 (m, 1H), 3.38 (br s, 4H), 2.66 (br s, 4H),2.19-2.10 (m, 1H), 1.79-1.73 (m, 1H), 1.35-1.28 (m, 1H); LCMS(electrospray) m/z 489.1 (M + H)+. B (1S,2S)-N-(6-(5-chloro-6-fluoro-7-(piperazin-1-yl)-1H-indazol-4- yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide. 3 TFA 77

¹H NMR (400 MHz, DMSO-d₆) δ 13.18 (s, 1H), 12.78 (s, 1H), 8.08 (s, 1H),7.84 (d, J = 8.4 Hz, 1H), 7.73 (s, 1H), 7.51 (d, J = 8.4 Hz, 1H),5.12-4.96 (m, 1H), 3.65 (br s, 4H), 2.19-2.10 (m, 1H), 1.95 (br s, 4H),1.77-1.73 (m, 1H), 1.35-1.28 (m, 1H); LCMS (electrospray) m/z 473.1 (M +H)+. B (1S,2S)-N-(6-(5-chloro-6-fluoro-7-(pyrrolidin-1-yl)-1H-indazol-4- yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 78

¹H NMR (400 MHz, DMSO-d₆) δ 13.17 (s, 1H), 12.79 (s, 1H), 8.09 (s, 1H),7.85 (d, J = 8.4 Hz, 1H), 7.75 (s, 1H), 7.83 (d, J = 6.4, Hz, 1H),5.14-4.97 (m, 2H), 4.41 (s, 1H), 3.97 (s, 2H), 3.73-3.35 (m, 2H),2.29-2.18 (m, 1H), 2.10-1.98 (m, 1H), 1.94- 1.85 (m, 1H), 1.82-1.70 (m,1H), 1.38-1.27 (m, 1H); LCMS (electrospray) m/z 490.10 (M + H)+. B(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(3-hydroxypyrrolidin-1-yl)-1H-indazol-4- yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 79

¹H NMR (400 MHz, DMSO-d₆) δ 13.75 (s, 1H), 12.84 (s, 1H), 8.20 (s, 1H),7.94-7.82 (m, 2H), 7.60 (d, J = 8.4 Hz, 1H), 7.83 (d, J = 6.4, Hz, 1H),5.18-4.87 (m, 2H), 3.52 (q, J = 5.2 Hz, 2H), 3.06 (t, J = 5.6 Hz, 2H),2.29-2.18 (m, 1H), 1.83-1.69 (m, 1H), 1.39-1.27 (m, 1H); LCMS(electrospray) m/z 481.05 (M + H)+. B(1S,2S)-N-(6-(5-chloro-6-fluoro-7-((2- hydroxyethyl)thio)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide 80

¹H NMR (400 MHz, DMSO-d₆) δ 13.78 (br s, 1H), 12.81 (s, 1H), 8.14 (d, J= 1.4 Hz, 1H), 7.88 (d, J = 8.4 Hz, 1H), 7.86-7.79 (m, 1H), 7.55 (dd, J= 1.8, 8.4 Hz, 1H), 5.25-4.85 (m, 1H), 4.15 (s, 3H), 2.30- 2.18 (m, 1H),1.85-1.68 (m, 1H), 1.33 (tdd, J = 6.4, 9.0, 12.7 Hz, 1H); LCMS(electrospray) m/z 435.3 (M + H)+. B (1S,2S)-N-(6-(5-chloro-6-fluoro-7-methoxy-1H-indazol-4-yl)benzo[d]thiazol- 2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 81

¹H NMR (400 MHz, DMSO-d₆) δ13.77 (s, 1H), 12.82 (s, 1H), 8.16 (d, J =1.5 Hz, 1H), 7.92-7.87 (m, 1H), 7.84-7.80 (m, 1H), 7.62-7.53 (m, 1H),5.27-4.92 (m, 1H), 4.38 (q, J = 7.0 Hz, 2H), 2.30- 2.20 (m, 1H),1.88-1.71 (m, 1H), 1.42 (t, J = 7.0 Hz, 3H), 1.38-1.29 (m, 1H); LCMS(electrospray) m/z 449.1 (M + H)+. B(1S,2S)-N-(6-(5-chloro-7-ethoxy-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 82

¹H NMR (400 MHz, DMSO-d₆) δ 7.91 (s, 1H), 7.74 (s, 1H), 7.66 (d, J = 8.4Hz, 1H), 7.40 (dd, J = 1.6, 6.8, Hz, 1H), 5.02-4.78 (m, 1H), 3.23 (t, J= 5.6 Hz, 2H), 2.99 (d, J = 4 Hz, 3H), 2.80 (t, J = 6.0 2H), 2.09-1.99(m, 1H), 1.74-1.62 (m, 1H), 1.16-1.07 (m, 1H); LCMS (electrospray) m/z477.10 (M + H)+. B (1S,2S)-N-(6-(7-((2-aminoethyl)(methyl)amino)-5-chloro-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 83

¹H NMR (400 MHz, DMSO-d₆) δ 8.07 (d, J = 1.6 Hz, 1H), 7.82 (d, J = 8.0Hz, 1H), 7.78 (s, 1H), 7.51 (dd, J = 2.0, 6.4 Hz, 1H), 5.14-4.91 (m,1H), 3.48 (m, 2H), 3.16 (t, J = 12 Hz 2H), 2.87-2.78(m, 1H), 2.24-2.15(m, 1H), 1.85 (d, J = 10.4 Hz, 2H), 1.80- 1.68 (m, 1H), 1.66-1.54 (m,2H), 1.33-1.24 (m, 1H); LCMS (electrospray) m/z 503.10 (M + H)+. B(1S,2S)-N-(6-(7-(4-aminopiperidin-1-yl)- 5-chloro-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide 84

¹H NMR (400 MHz, DMSO-d₆) δ 8.10 (d, J = 1.6 Hz, 1H), 7.85 (d, J = 8.4Hz, 1H), 7.79 (s, 1H), 7.53 (dd, J = 1.6, 8.0 Hz, 1H), 5.15-4.93 (m,1H), 3.26- 3.17 (m, 2H), 3.12-2.96 (m, 2H), 2.89-2.81 (m, 1H), 2.26-2.17(m, 1H), 1.91-1.68 (m, 4H), 1.35- 1.23 (m, 2H); LCMS (electrospray) m/z503.1 (M + H)+. B (1S,2S)-N-(6-(7-(3-aminopiperidin-1-yl)-5-chloro-6-fluoro-1H-indazol-4- yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 85

¹H NMR (400 MHz, DMSO-d₆) δ 13.94 (s, 1H), 12.83 (s, 1H), 8.15 (s, 1H),7.89 (d, J = 8.0 Hz, 1H), 7.82 (s, 1H), 7.56 (d, J = 8.0 Hz, 1H),5.14-4.97 (m, 1H), 3.61 (s, 3H), 3.41-3.38 (m, 2H), 2.87- 2.84 (m, 2H),2.78 (s, 6H), 2.26-2.23 (m, 1H), 1.73- 1.65 (m, 1H), 1.31-1.23 (m, 1H);LCMS (electrospray) m/z 505.1 (M + H)+. B (1S,2S)-N-(6-(5-chloro-7-((2-(dimethylamino)ethyl)(methyl)amino)-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide. 3 HCl 86

¹H NMR (400 MHz, DMSO-d₆) δ 13.94 (s, 1H), 12.85 (s, 1H), 8.19 (s, 1H),7.89 (d, J = 8.0 Hz, 1H), 7.82 (s, 1H), 7.60 (d, J = 8.0 Hz, 1H),5.14-4.97 (m, 1H), 3.61-3.57 (m, 2H), 3.04-3.01 (m, 2H), 2.87-2.84 (m,2H), 2.26-2.23 (m, 1H), 1.73-1.65 (m, 1H), 1.64-1.61 (m, 2H), 1.31-1.23(m, 1H); LCMS (electrospray) m/z 495.1 (M + H)+. B(1S,2S)-N-(6-(5-chloro-6-fluoro-7-((3- hydroxypropyl)thio)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropanecarboxamide. 2 HCl 87

¹H NMR (400 MHz, DMSO-d₆) δ 13.86 (s, 1H), 12.84 (s, 1H), 8.19 (d, J =1.6 Hz, 1H), 8.13-8.05 (m, 1H), 7.95-7.85 (m, 2H), 7.59 (dd, J = 1.6,8.4 Hz, 1H), 5.18-4.95 (m, 1H), 3.66 (s, 2H), 2.58 (d, J = 1.4 Hz, 3H),2.29-2.21 (m, 1H), 1.83-1.69 (m, 1H), 1.38-1.28 (m, 1H); LCMS(electrospray) m/z 509.1 (M + H)+. B(1S,2S)-N-(6-(5-chloro-6-fluoro-7-((2-(methylamino)-2-oxoethyl)thio)-1H- indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropanecarboxamide 88

¹H NMR (400 MHz, DMSO-d₆) δ 13.56 (s, 1H), 12.83 (s, 1H), 8.19 (d, J =1.6 Hz, 1H), 7.93-7.81 (m, 2H), 7.59 (dd, J = 2.0, 8.0 Hz, 1H), 7.20 (s,1H), 5.17-4.95 (m, 2H), 4.01 (s, J = 8.8 Hz, 1H), 3.91-3.82 (m, 1H),3.67-3.60 (m, 1H), 3.55 (t, J = 5.2 Hz, 2H), 2.29-2.21 (m, 1H),1.83-1.70 (m, 1H), 1.38-1.28 (m, 1H); LCMS (electrospray) m/z 519.1 (M +H)+. B (1-(5-chloro-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)benzo[d]thiazol-6-yl)-1H-indazol-7-yl)azetidin-3-yl)carbamic acid 89

¹H NMR (400 MHz, DMSO-d₆) δ 13.25 (s, 1H), 12.78 (s, 1H), 8.09 (d, J =1.6 Hz, 1H), 7.90-7.70 (m, 2H), 7.52 (dd, J = 1.6, 8.4 Hz, 1H), 7.20 (s,1H), 5.67-5.47 (s, 1H), 5.17-4.93 (m, 1H), 4.43- 4.16 (m, 2H), 4.04-3.96(m, 1H), 3.89-3.52 (m, 2H), 2.86 (s, 3H), 2.29-2.20 (m, 1H), 1.83-1.68(m, 1H), 1.38-1.27 (m, 1H); LCMS (electrospray) m/z 533.1 (M + H)+ B(1-(5-chloro-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)benzo[d]thiazol-6-yl)-1H- indazol-7-yl)azetidin-3-yl)(methyl)carbamic acid 90

¹H NMR (400 MHz, DMSO-d₆) δ 13.13 (s, 1H), 12.78 (s, 1H), 8.10 (d, J =1.6 Hz, 1H), 7.89-7.68 (m, 2H), 7.52 (dd, J = 2.4, 8.8 Hz, 1H), 7.21 (s,1H), 5.82-5.62 (s, 1H), 5.17-4.94 (m, 1H), 4.33- 4.23 (m, 1H), 4.15-4.06(m, 1H), 3.67-3.43 (m, 2H), 3.34-3.26 (m, 1H), 3.12-3.05 (m, 1H), 2.31-2.15 (m, 2H), 1.84-1.69 (m, 1H), 1.39-1.26 (m, 1H); LCMS (electrospray)m/z 533.1 (M + H)+. B ((1-(5-chloro-6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1- carboxamido)benzo[d]thiazol-6-yl)-1H-indazol-7-yl)azetidin-3- yl)methyl)carbamic acid 91

¹H NMR (400 MHz, DMSO-d₆) δ 7.85 (s, 1H), 7.76 (s, 1H), 7.63 (d, J = 8.4Hz, 1H), 7.36 (dd, J = 1.6, 8.4 Hz, 1H), 5.02-4.78 (m, 1H), 4.04-3.87(m, 1H), 3.78-3.61 (m, 2H), 3.58-3.48 (m, 1H), 2.72-2.59 (m, 2H),2.34-2.26 (m, 1H), 2.09-1.92 (m, 2H), 1.74-1.61 (m, 4H), 1.15-1.02 (m,1H); LCMS (electrospray) m/z 503.1 (M + H)+. B (1S,2S)-N-(6-(7-(3-(aminomethyl)pyrrolidin-1-yl)-5-chloro-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropanecarboxamide 92

¹H NMR (400 MHz, DMSO-d₆) δ 13.42 (s, 1H), 12.82 (s, 1H), 8.22 (s, 1H),8.14 (s, 1H), 7.90 (d, J = 8.0 Hz, 1H), 7.85 (s, 1H), 7.55 (d, J = 8.0Hz, 1H), 5.14-4.97 (m, 1H), 2.89 (m, 2H), 2.65 (t, J = 5.2 Hz, 2H),2.26-2.23 (m, 1H), 1.73-1.65 (m, 1H), 1.31-1.23 (m, 1H); LCMS(electrospray) m/z 491.1 (M + H)+. B (1S,2S)-N-(6-(5-chloro-6-fluoro-7-(methyl(2-(methylamino)ethyl)amino)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide93

¹H NMR (400 MHz, DMSO-d₆) δ 13.42 (s, 1H), 12.81 (s, 1H), 8.22 (s, 1H),8.14 (s, 1H), 7.87 (d, J = 8.4 Hz, 1H), 7.78 (s, 1H), 7.55 (d, J = 8.8Hz, 1H), 5.14-4.96 (m, 1H), 3.64-3.61 (m, 2H), 3.35- 3.32 (m, 2H), 3.02(s, 3H), 2.26-2.23 (m, 1H), 1.73- 1.65 (m, 1H), 1.31-1.23 (m, 1H); LCMS(electrospray) m/z 478.1 (M + H)+. B(1S,2S)-N-(6-(5-chloro-6-fluoro-7-((2-hydroxyethyl)(methyl)amino)-1H-indazol- 4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropanecarboxamide. 2 HCl 94

¹H NMR (400 MHz, DMSO-d₆) δ 13.51 (s, 1H), 12.82 (s, 1H), 8.49 (br, 1H),8.38 (br, 1H), 8.14 (s, 1H), 7.89 (d, J = 8.4 Hz, 1H), 7.72 (s, 1H),7.55 (d, J = 8.8 Hz, 1H), 5.16-4.97 (m, 1H), 3.96-3.91 (m, 2H),3.67-3.64 (m, 2H), 2.90 (s, 3H), 2.26-2.23 (m, 1H), 1.79-1.72 (m, 1H),1.37-1.30 (m, 1H), 1.08 (t, J = 7.2 Hz, 1H); LCMS (electrospray) m/z503.1 (M + H)+. B (1S,2S)-N-(6-(7-((azetidin-3-ylmethyl)(methyl)amino)-5-chloro-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropanecarboxamide. 3 TFA 95

¹H NMR (400 MHz, DMSO-d₆) δ 13.18 (s, 1H), 12.78 (s, 1H), 8.57 (br, 2H),8.08 (s, 1H), 7.85 (d, J = 8.4 Hz, 1H), 7.77 (s, 1H), 7.51 (dd, J = 8.0Hz, J = 1.6 Hz, 1H), 5.16-4.95 (m, 1H), 4.00 (m, 2H), 3.92 (m, 2H), 3.71(br, 2H), 3.05 (br, 1H), 2.25- 2.20 (m, 1H), 1.78-1.68 (m, 1H),1.36-1.28 (m, 1H), 1.08 (t, J = 7.2 Hz, 1H); LCMS (electrospray) m/z489.1 (M + H)+. B (1S,2S)-N-(6-(7-((azetidin-3-ylmethyl)amino)-5-chloro-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropanecarboxamide. 3TFA 96

¹H NMR (400 MHz, DMSO-d₆) δ 13.26 (br s, 1H), 12.74 (s, 1H), 8.00 (d, J= 1.4 Hz, 1H), 7.83 (d, J = 8.3 Hz, 1H), 7.60 (s, 1H), 7.44 (dd, J =1.7, 8.3 Hz, 1H), 6.81 (s, 1H), 5.16-4.94 (m, 1H), 3.98 (s, 3H), 2.31(s, 3H), 2.27-2.19 (m, 1H), 1.82-1.68 (m, 1H), 1.32 (tdd, J = 6.3, 9.0,12.8 Hz, 1H); LCMS(electrospray) m/z 397.4 (M + H+). B(1S,2S)-2-fluoro-N-(6-(7-methoxy-5-methyl-1H-indazol-4-yl)benzo[d]thiazol- 2-yl)cyclopropanecarboxamide. 2TFA 97

¹H NMR (400 MHz, DMSO-d₆) δ 13.44 (br s, 1H), 12.76 (s, 1H), 8.04 (d, J= 1.3 Hz, 1H), 7.86 (d, J = 8.3 Hz, 1H), 7.69 (s, 1H), 7.46 (dd, J =1.7, 8.3 Hz, 1H), 5.18-4.89 (m, 1H), 4.08 (d, J = 0.9 Hz, 3H), 2.29-2.22(m, 1H), 2.20 (d, J = 3.2 Hz, 3H), 1.83-1.69 (m, 1H), 1.32 (tdd, J =6.4, 8.8, 12.8 Hz, 1H); LCMS(electrospray) m/z 415.4 (M + H+). B(1S,2S)-2-fluoro-N-(6-(6-fluoro-7- methoxy-5-methyl-1H-indazol-4-yl)benzo[d]thiazol-2- yl)cyclopropanecarboxamide. 2 TFA 98

¹H NMR (400 MHz, DMSO-d₆) 13.42 (br s, 1H), 12.78 (s, 1H), 8.05 (d, J =1.3 Hz, 1H), 7.86 (d, J = 8.3 Hz, 1H), 7.68 (s, 1H), 7.47 (dd, J = 1.5,8.3 Hz, 1H), 5.22-4.90 (m, 1H), 4.30 (br d, J = 7.1 Hz, 2H), 2.23 (br d,J = 7.0 Hz, 1H), 2.19 (d, J = 3.1 Hz, 3H), 1.80-1.70 (m, 1H), 1.39 (t, J= 7.0 Hz, 3H), 1.35-1.28 (m, 1H); LCMS(electrospray) m/z 429.4 (M + H+).B (1S,2S)-N-(6-(7-ethoxy-6-fluoro-5-methyl-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropanecatboxamide. 2 TFA 99

¹H NMR (400 MHz, DMSO-d₆) δ 13.76 (s, 1H), 12.84 (s, 1H), 8.19 (d, J =2.0 Hz, 1H), 7.94-7.84 (m, 2H), 7.59 (dd, J = 1.6, 8.0 Hz, 1H),5.17-4.95 (m, 1H), 4.03 (s, 2H), 3.01 (s, 3H), 2.81 (s, 3H), 2.29-2.20(m, 1H), 1.82-1.70 (m, 1H), 1.38-1.28 (m, 1H); LCMS (electrospray) m/z522.10 (M + H)+. B (1S,2S)-N-(6-(5-chloro-7-((2-(dimethylamino)-2-oxoethyl)thio)-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 100

¹H NMR (400 MHz, DMSO-d₆) δ 13.42 (s, 1H), 12.80 (s, 1H), 8.12 (s, 1H),7.87 (d, J = 8.4 Hz, 1H), 7.77 (s, 1H), 7.54 (dd, J = 8.0 Hz, J = 1.6Hz, 1H), 5.14-4.96 (m, 1H), 3.62 (s, 2H), 3.37 (s, 6H), 3.15 (s, 3H),2.25-2.20 (m, 1H), 1.78-1.68 (m, 1H), 1.34-1.28 (m, 1H); LCMS(electrospray) m/z 519.1 (M + H)+. B (1S,2S)-N-(6-(5-chloro-7-((2-(dimethylamino)-2- oxoethyl)(methyl)amino)-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide101

¹H NMR (400 MHz, DMSO-d₆) δ 13.22 (br s, 1H), 12.74 (s, 1H), 8.00 (d, J= 1.3 Hz, 1H), 7.83 (d, J = 8.3 Hz, 1H), 7.60 (s, 1H), 7.44 (dd, J =1.8, 8.3 Hz, 1H), 6.79 (s, 1H), 5.17-4.93 (m, 1H), 4.27 (q, J = 7.1 Hz,2H), 2.29 (s, 3H), 2.27-2.20 (m, 1H), 1.82- 1.69 (m, 1H), 1.46 (t, J =7.0 Hz, 3H), 1.32 (tdd, J = 6.4, 8.9, 12.8 Hz, 1H); LCMS(electrospray)m/z 410.9 (M + H+). B (1S,2S)-N-(6-(7-ethoxy-5-methyl-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide.2 TFA 102

¹H NMR (400 MHz, DMSO-d₆) δ 13.16 (br s, 1H), 12.77 (s, 1H), 8.00 (d, J= 1.6 Hz, 1H), 7.85 (d, J = 8.3 Hz, 1H), 7.55 (s, 1H), 7.42 (dd, J =1.6, 8.3 Hz, 1H), 5.18-4.93 (m, 1H), 2.96 (s, 3H), 2.96 (s, 3H),2.56-2.52 (m, 2H), 2.29-2.20 (m, 1H), 1.82- 1.71 (m, 1H), 1.32 (tdd, J =6.6, 9.0, 12.8 Hz, 1H), 1.07 (t, J = 7.4 Hz, 3H); LCMS(electrospray) m/z442.2 (M + H+). B (1S,2S)-N-(6-(7-(dimethylamino)-5-ethyl-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol- 2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 103

¹H NMR (400 MHz, DMSO-d₆) δ 13.44 (br s, 1H), 12.80 (s, 1H), 8.05 (d, J= 1.3 Hz, 1H), 7.88 (d, J = 8.1 Hz, 1H), 7.64 (s, 1H), 7.45 (dd, J =1.8, 8.3 Hz, 1H), 5.18-4.92 (m, 1H), 2.59 (br d, J = 6.9 Hz, 2H), 2.52(br s, 3H), 2.29-2.20 (m, 1H), 1.82- 1.70 (m, 1H), 1.37-1.28 (m, 1H),1.08 (t, J = 7.3 Hz, 3H); LCMS(electrospray) m/z 445.3 (M + H+). B(1S,2S)-N-(6-(5-ethyl-6-fluoro-7- (methylthio)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide. 2 TFA 104

¹H NMR (400 MHz, DMSO-d₆) δ 13.15 (br s, 1H), 12.77 (br s, 1H), 8.03 (s,1H), 7.85 (d, J = 8.3 Hz, 1H), 7.64 (s, 1H), 7.46 (br d, J = 8.3 Hz,1H), 5.18- 4.89 (m, 1H), 2.95 (s, 6H), 2.28-2.22 (m, 1H), 2.16 (br d, J= 3.2 Hz, 3H), 1.83-1.69 (m, 1H), 1.38- 1.24 (m, 1H); LCMS(electrospray)m/z 428.2 (M + H+). B (1S,2S)-N-(6-(7-(dimethylamino)-6-fluoro-5-methyl-1H-indazol-4- yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 105

¹H NMR (400 MHz, CHLOROFORM-d) δ 12.79 (br s, 1H), 8.09 (d, J = 1.6 Hz,1H), 7.86 (d, J = 8.3 Hz, 1H), 7.71 (s, 1H), 7.51 (dd, J = 1.8, 8.3 Hz,1H), 7.48 (d, J = 9.3 Hz, 1H), 5.21-4.92 (m, 1H), 2.28-2.22 (m, 1H),2.21 (s, 3H), 1.83-1.69 (m, 1H), 1.32 (ddd, J = 2.6, 6.4, 12.8 Hz, 1H);LCMS(electrospray) m/z 417.1 (M + H+). B(1S,2S)-2-fluoro-N-(6-(6-fluoro-5- (methylthio)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)cyclopropane-1- carboxamide. 2 TFA 106

¹H NMR (400 MHz, DMSO-d₆) δ 13.84 (br s, 1H), 12.79 (s, 1H), 8.03 (d, J= 1.6 Hz, 1H), 7.88 (d, J = 8.3 Hz, 1H), 7.70 (br s, 1H), 7.43 (dd, J =1.8, 8.3 Hz, 1H), 5.23-4.89 (m, 1H), 2.61 (br d, J = 6.0 Hz, 2H),2.29-2.20 (m, 1H), 1.82-1.69 (m, 1H), 1.37- 1.27 (m, 1H), 1.09 (t, J =7.4 Hz, 3H); LCMS(electrospray) m/z 417.1 (M + H+). B(1S,2S)-N-(6-(5-ethyl-6,7-difluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide.2 TFA 107

¹H NMR (400 MHz, DMSO-d₆) δ 13.43 (s, 1H), 12.78 (s, 1H), 8.02 (s, 1H),7.87 (d, J = 8.4 Hz, 1H), 7.59 (s, 1H), 7.45-7.42 (m, 1H), 5.15-4.97 (m,1H), 4.34-4.28 (m, 2H), 2.59-2.53 (m, 2H), 2.27- 2.23 (m, 1H), 1.85-1.75(m, 1H), 1.40 (t, J = 6.8 Hz, 3H), 1.36-1.32 (m, 1H), 1.09 (t, J = 7.2Hz, 3H); LCMS(electrospray) m/z 443.2 (M + H+). B(1S,2S)-N-(6-(7-ethoxy-5-ethyl-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 108

¹H NMR (400 MHz, DMSO-d₆) δ 13.27 (s, 1H), 12.82 (s, 1H), 10.11 (s, 1H),8.20 (d, J = 1.6 Hz, 1H), 7.91 (d, J = 8.4 Hz, 1H), 7.81 (d, J = 1.1 Hz,1H), 7.60 (dd, J = 1.7, 8.3 Hz, 1H), 5.18-4.96 (m, 1H), 2.26 (ddd, J =2.2, 4.5, 6.5 Hz, 1H), 2.19 (s, 3H), 1.77 (tdd, J = 3.2, 6.8, 19.9 Hz,1H), 1.33 (tdd, J = 6.3, 9.0, 12.8 Hz, 1H); LCMS(electrospray) m/z 462.1(M + H+). B (1S,2S)-N-(6-(7-acetamido-5-chloro-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide. 1 TFA 109

¹H NMR (400 MHz, DMSO-d₆) δ 14.35-13.37 (m, 1H), 12.79 (s, 1H), 8.07 (d,J = 1.6 Hz, 1H), 7.88 (d, J = 8.3 Hz, 1H), 7.79 (br s, 1H), 7.48 (dd, J= 1.8, 8.3 Hz, 1H), 5.22-4.90 (m, 1H), 2.27-2.19 (m, 4H), 1.83-1.69 (m,1H), 1.32 (tdd, J = 6.4, 9.0, 12.9 Hz, 1H); LCMS(electrospray) m/z 403.2(M + H+). B (1S,2S)-N-(6-(6,7-difluoro-5-methyl-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide110

¹H NMR (400 MHz, DMSO-d₆) δ 13.36 (br s, 1H), 12.77 (s, 1H), 8.04 (d, J= 1.5 Hz, 1H), 7.84 (d, J = 8.3 Hz, 1H), 7.67 (s, 1H), 7.48 (dd, J =1.7, 8.3 Hz, 1H), 5.16-4.94 (m, 1H), 2.97 (d, J = 2.1 Hz, 6H), 2.27-2.22(m, 1H), 2.20 (s, 3H), 1.83-1.69 (m, 1H), 1.39-1.26 (m, 1H);LCMS(electrospray) m/z 460 (M + H+). B(1S,2S)-N-(6-(7-(dimethylamino)-6- fluoro-5-(methylthio)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide. 1 TFA 111

¹H NMR (400 MHz, DMSO-d₆) δ 13.77-13.52 (m, 1H), 12.80 (s, 1H), 8.09 (d,J = 1.5 Hz, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.78 (s, 1H), 7.52 (dd, J =1.8, 8.3 Hz, 1H), 5.20-4.93 (m, 1H), 2.55 (s, 3H), 2.30-2.24 (m, 1H),2.22 (s, 3H), 1.83-1.70 (m, 1H), 1.32 (tdd, J = 6.4, 8.9, 12.8 Hz, 1H);LCMS(electrospray) m/z 462.05 (M + H+). B(1S,2S)-2-fluoro-N-(6-(6-fluoro-5,7- bis(methylthio)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)cyclopropane-1- carboxamide. 1 TFA 112

¹H NMR (400 MHz, DMSO-d₆) δ 13.16 (s, 1H), 12.83 (s, 1H), 8.14 (d, J =1.5 Hz, 1H), 7.92 (d, J = 8.3 Hz, 1H), 7.85 (d, J = 1.2 Hz, 1H), 7.53(dd, J = 1.7, 8.3 Hz, 1H), 5.19-4.94 (m, 1H), 3.50 (s, 3H), 2.29 (br s,1H), 2.24 (d, J = 2.9 Hz, 3H), 1.85-1.69 (m, 1H), 1.41-1.24 (m, 1H);LCMS(electrospray) m/z 463.1 (M + H+). B(1S,2S)-2-fluoro-N-(6-(6-fluoro-5-methyl-7-(methylsulfonyl)-1H-indazol-4- yl)benzo[d]thiazol-2-yl)cyclopropane-1-carboxamide 113

¹H NMR (400 MHz, DMSO-d₆) δ 12.94-12.86 (m, 1H), 12.83-12.74 (m, 1H),9.90 (br s, 1H), 8.09 (br s, 1H), 7.88 (br d, J = 7.9 Hz, 1H), 7.66 (brs, 1H), 7.49 (br d, J = 7.4 Hz, 1H), 5.19-4.95 (m, 1H), 2.28-2.23 (m,1H), 2.20 (br s, 3H), 2.16 (br s, 3H), 1.84-1.69 (m, 1H), 1.42-1.25 (m,1H); LCMS(electrospray) m/z 442.0 (M + H+). B(1S,2S)-N-(6-(7-acetamido-6-fluoro-5-methyl-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 114

¹H NMR (400 MHz, DMSO-d₆) δ 13.05 (s, 1H), 10.78 (s, 1H), 8.08 (s, 1H),7.83 (d, J = 8.4 Hz, 1H), 7.72 (s, 1H), 7.12 (d, J = 8.0 Hz, 1H), 6.45(d, J = 12.4 Hz, 1H), 5.14-4.95 (m, 1H), 3.37 (s, 3H), 2.25-2.20 (m,1H), 1.78-1.68 (m, 1H), 1.34-1.28 (m, 10H); LCMS (electrospray) m/z549.1 (M + H)+. B tert-butyl 2-(5-chloro-6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1- carboxamido)benzo[d]thiazol-6-yl)-1H-indazol-7-yl)-1-methylhydrazine-1- carboxylate 115

¹H NMR (400 MHz, DMSO-d₆) δ 12.88 (s, 1H), 12.79 (s, 1H), 8.25 (s, 1H),8.11 (s, 1H), 7.89 (d, J = 8.4 Hz, 1H), 7.76 (s, 1H), 7.52 (d, J = 8.0Hz, 1H), 6.45 (d, J = 12.4 Hz, 1H), 5.13-4.96 (m, 1H), 4.04-3.99 (m,1H), 3.23 (s, 3H), 2.25-2.20 (m, 1H), 1.78-1.68 (m, 1H), 1.34-1.28 (m,1H); LCMS (electrospray) m/z 449.1 (M + H)+. B(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(2- methylhydrazineyl)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide 116

¹H NMR (400 MHz, DMSO-d₆) δ 13.28 (s, 1H), 12.87-12.78 (m, 1H), 8.14 (d,J = 1.5 Hz, 1H), 7.91 (d, J = 8.3 Hz, 1H), 7.80 (d, J = 1.3 Hz, 1H),7.53 (dd, J = 1.8, 8.4 Hz, 1H), 5.18-4.95 (m, 1H), 3.98 (s, 3H), 2.21(d, J = 3.1 Hz, 3H), 1.91-1.88 (m, 1H), 1.69 (br d, J = 2.8 Hz, 1H),1.34-1.29 (m, 1H); LCMS(electrospray) m/z 443.1(M + H+). B methyl6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)benzo[d]thiazol-6-yl)-5- methyl-1H-indazole-7-carboxylate. 1TFA 117

¹H NMR (400 MHz, DMSO-d₆) δ 14.07 (br s, 1H), 12.81 (s, 1H), 8.08 (d, J= 1.5 Hz, 1H), 7.86 (d, J = 8.4 Hz, 2H), 7.50 (dd, J = 1.8, 8.3 Hz, 1H),5.19- 4.94 (m, 1H), 2.29-2.20 (m, 4H), 1.84-1.68 (m, 1H), 1.38-1.26 (m,1H); LCMS(electrospray) m/z 435.1 (M + H+). B(1S,2S)-N-(6-(6,7-difluoro-5-(methylthio)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 2,2,2- trifluoroacetate. 1 TFA 118

¹H NMR (400 MHz, DMSO-d₆) δ 13.87-13.43 (m, 1H), 12.78 (s, 1H), 8.07 (s,1H), 7.85 (d, J = 8.4 Hz, 1H), 7.73 (s, 1H), 7.50 (dd, J = 1.3, 8.4 Hz,1H), 5.21-4.93 (m, 1H), 4.35 (q, J = 7.0 Hz, 2H), 2.30-2.19 (m, 4H),1.84-1.70 (m, 1H), 1.41 (t, J = 7.0 Hz, 3H), 1.37-1.27 (m, 1H);LCMS(electrospray) m/z 461.2 (M + H+). B(1S,2S)-N-(6-(7-ethoxy-6-fluoro-5- (methylthio)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide. 1 TFA 119

¹H NMR (400 MHz, DMSO-d₆) δ 13.47 (br s, 1H), 12.87 (s, 1H), 8.24 (d, J= 1.6 Hz, 1H), 8.00 (s, 1H), 7.94 (d, J = 8.4 Hz, 1H), 7.62 (dd, J =1.8, 8.4 Hz, 1H), 5.17-4.95 (m, 1H), 3.56 (s, 3H), 2.29-2.22 (m, 1H),1.83-1.71 (m, 1H), 1.37-1.29 (m, 1H); LCMS(electrospray) m/z 483 (M +H+). B (1S,2S)-N-(6-(5-chloro-6-fluoro-7- (methylsulfonyl)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide 120

¹H NMR (400 MHz, DMSO-d₆) δ 11.22-11.13 (m, 1H), 8.66 (d, J = 7.1 Hz,1H), 7.95-7.87 (m, 1H), 7.72-7.70 (m, 1H), 6.96-6.93 (m, 1H), 6.92- 6.89(m, 1H), 5.07-4.81 (m, 1H), 3.21 (s, 3H), 2.30-2.25 (m, 3H), 2.25-2.23(m, 1H), 2.20-2.09 (m, 1H), 1.79 (s, 3H), 1.74-1.63 (m, 1H), 1.28- 1.09(m, 1H); LCMS(electrospray) m/z 456.1 (M + H+) B(1S,2S)-2-fluoro-N-(6-(6-fluoro-5-methyl-7-(N-methylacetamido)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)cyclopropane-1- carboxamide. 1 TFA 121

¹H NMR (400 MHz, DMSO-d₆) δ 13.45 (br s, 1H), 12.85 (s, 1H), 8.23 (d, J= 1.6 Hz, 1H), 7.94-7.88 (m, 2H), 7.62 (dd, J = 1.8, 8.4 Hz, 1H),5.21-4.90 (m, 1H), 2.29-2.17 (m, 1H), 1.85-1.62 (m, 1H), 1.42-1.26 (m,1H); LCMS(electrospray) m/z 449.2 (M + H+). B5-chloro-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)benzo[d]thiazol-6-yl)-1H- indazole-7-carboxylic acid. 1 TFA122

¹H NMR (400 MHz, DMSO-d₆) δ 13.57 (s, 1H), 12.86 (s, 1H), 8.36-8.16 (m,1H), 7.96-7.91 (m, 2H), 7.63 (dd, J = 1.8, 8.4 Hz, 1H), 5.22-4.90 (m,1H), 4.00 (s, 3H), 2.30-2.20 (m, 1H), 1.83-1.68 (m, 1H), 1.45-1.21 (m,1H); LCMS(electrospray) m/z 463.1 (M + H+). B methyl5-chloro-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)benzo[d]thiazol-6-yl)-1H- indazole-7-carboxylate. 1 TFA 123

¹H NMR (400 MHz, DMSO-d₆) δ 14.06-13.79 (m, 1H), 12.83 (s, 1H), 8.21 (d,J = 1.6 Hz, 1H), 7.91-7.89 (m, 1H), 7.63 (d, J = 1.7 Hz, 1H), 7.62- 7.59(m, 1H), 5.15-4.96 (m, 1H), 3.23 (s, 3H), 2.27-2.23 (m, 1H), 1.82 (s,3H), 1.76-1.69 (m, 1H), 1.36-1.30 (m, 1H); LCMS(electrospray) m/z 476.1(M + H+). B (1S,2S)-N-(6-(5-chloro-6-fluoro-7-(N-methylacetamido)-1H-indazol-4- yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide. 1 TFA 124

¹H NMR (400 MHz, DMSO-d₆) δ 12.94 (br s, 1H), 8.10 (d, J = 1.5 Hz, 1H),7.91(d, J = 8.3 Hz, 1H), 7.68 (s, 1H), 7.51 (dd, J = 1.7, 8.3 Hz, 1H),5.19- 4.92 (m, 1H), 2.31-2.25 (m, 1H), 2.19 (d, J = 3.1 Hz, 3H),1.82-1.71 (m, 1H), 1.37-1.28 (m, 1H); LCMS(electrospray) m/z 429.1(M +H+). B 6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)benzo[d]thiazol-6-yl)-5- methyl-1H-indazole-7-carboxylicacid 125

¹H NMR (400 MHz, DMSO-d₆) δ 13.86-13.55 (m, 1H), 8.21 (d, J = 1.5 Hz,1H), 7.92 (s, 1H), 7.90 (s, 1H), 7.61 (dd, J = 1.8, 8.4 Hz, 1H),5.17-4.94 (m, 1H), 3.13 (s, 3H), 2.94 (s, 3H), 2.28-2.22 (m, 1H),1.81-1.72 (m, 1H), 1.36-1.28 (m, 1H); LCMS(electrospray) m/z 475.9 (M +H+). B 5-chloro-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)benzo[d]thiazol-6-yl)-N,N-dimethyl-1H-indazole-7-carboxamide 126

¹H NMR (400 MHz, DMSO-d₆) δ 8.16 (d, J = 1.6 Hz, 1H), 7.95 (d, J = 3.2Hz, 1H), 7.89 (d, J = 8.3 Hz, 1H), 7.56 (dd, J = 1.8, 8.3 Hz, 1H),5.18-4.93 (m, 1H), 2.29-2.20 (m, 1H), 1.83-1.70 (m, 1H), 1.32 (tdd, J =6.4, 9.0, 12.8 Hz, 1H); LCMS(electrospray) m/z 423.1 (M + H+). B(1S,2S)-N-(6-(5-chloro-6,7-difluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide127

¹H NMR (400 MHz, DMSO-d₆) δ 13.71-13.47 (s, 1H), 12.98-12.70 (s, 1H),8.65-8.55 (s, 1H), 8.21 (s, 1H), 7.97-7.88 (m, 1H), 7.85 (s, 1H), 7.63-7.56 (m, 1H), 5.20-4.91 (m, 1H), 2.91 (br d, J = 4.3 Hz, 3H), 2.30-2.21(m, 1H), 1.84-1.69 (m, 1H), 1.41-1.28 (m, 1H); LCMS(electrospray) m/z462.0 (M + H+). B 5-chloro-6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1- carboxamido)benzo[d]thiazol-6-yl)-N-methyl-1H-indazole-7-carboxamide 128

¹H NMR (400 MHz, DMSO-d₆) δ 13.69 (s, 1H), 12.86 (s, 1H), 8.24 (d, J =1.5 Hz, 1H), 7.97-7.87 (m, 2H), 7.63 (dd, J = 1.7, 8.4 Hz, 1H),5.22-4.92 (m, 1H), 2.77 (d, J = 6.2 Hz, 3H), 2.31-2.21 (m, 1H),1.83-1.70 (m, 1H), 1.25-1.32 (m, J = 2.5, 6.3, 12.8 Hz, 1H);LCMS(electrospray) m/z 447.2 (M + H+). B(1S,2S)-N-(6-(7-acetyl-5-chloro-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 129

¹H NMR (400 MHz, DMSO-d₆) δ 8.14 (s, 1H), 7.92-7.82 (m, 2H), 7.59-7.51(m, 1H), 5.18-4.92 (m, 1H), 4.51-4.40 (m, 1H), 4.11-3.85 (m, 3H), 2.94(s, 3H), 2.89-2.16 (m, 1H), 2.03-1.88 (m, 1H), 1.83-1.68 (m, 1H),1.38-1.27 (m, 1H); LCMS (electrospray) m/z 489.10 (M + H)+. B(1S,2S)-N-(6-(7-(azetidin-3- yl(methyl)amino)-5-chloro-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide130

¹H NMR (400 MHz, DMSO-d₆) δ 13.86-13.56 (m, 1H), 12.93-12.67 (m, 1H),8.01 (s, 1H), 7.82 (d, J = 8.3 Hz, 1H), 7.63 (s, 1H), 7.40 (br d, J =8.5 Hz, 1H), 5.20-4.90 (m, 1H), 3.01 (s, 6H), 2.28- 2.18 (m, 1H),1.82-1.69 (m, 1H), 1.31 (ddd, J = 2.4, 6.4, 12.5 Hz, 1H);LCMS(electrospray) m/z 482.1 (M + H+). B(1S,2S)-N-(6-(7-(dimethylamino)-6-fluoro-5-(trifluoromethyl)-1H-indazol-4- yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 131

¹H NMR (400 MHz, DMSO-d₆) δ 13.39 (s, 1H), 12.82 (br d, J = 1.7 Hz, 1H),8.13 (s, 1H), 7.91 (d, J = 8.3 Hz, 1H), 7.76 (s, 1H), 7.52 (dd, J = 1.4,8.3 Hz, 1H), 5.18-4.92 (m, 1H), 2.74 (d, J = 6.2 Hz, 3H), 2.24 (br d, J= 3.2 Hz, 3H), 1.86-1.66 (m, 1H), 1.32 (tdd, J = 6.5, 8.8, 12.7 Hz, 1H);LCMS(electrospray) m/z 427.10 (M + H+). B(1S,2S)-N-(6-(7-acetyl-6-fluoro-5-methyl-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 132

¹H NMR (400 MHz, DMSO-d₆) δ 13.19 (s, 1H), 12.81 (br s, 1H), 8.11 (d, J= 1.5 Hz, 1H), 7.90 (d, J = 8.3 Hz, 1H), 7.70 (d, J = 1.1 Hz, 1H), 7.50(dd, J = 1.7, 8.3 Hz, 1H), 5.18-4.93 (m, 1H), 2.90 (d, J = 4.5 Hz, 3H),2.29-2.24 (m, 1H), 2.22 (d, J = 3.1 Hz, 3H), 1.87-1.67 (m, 1H), 1.33(tdd, J = 6.4, 8.9, 12.7 Hz, 1H); LCMS(electrospray) m/z 442.1 (M + H+).B 6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)benzo[d]thiazol-6-yl)-N,5-dimethyl-1H-indazole-7-carboxamide 133

¹H NMR (400 MHz, DMSO-d₆) δ 13.45 (br s, 1H), 12.81 (s, 1H), 8.15 (d, J= 1.5 Hz, 1H), 7.89 (d, J = 8.4 Hz, 1H), 7.78 (s, 1H), 7.57 (dd, J =1.8, 8.4 Hz, 1H), 5.17-4.92 (m, 1H), 3.26 (q, J = 6.4 Hz, 2H), 2.98 (s,3H), 2.30-2.21 (m, 1H), 1.85-1.70 (m, 1H), 1.33 (tdd, J = 6.5, 8.8, 12.8Hz, 1H), 1.09 (t, J = 7.1 Hz, 3H); LCMS(electrospray) m/z 462.1(M + H+).B (1S,2S)-N-(6-(5-chloro-7- (ethyl(methyl)amino)-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2- fluorocyclopropane-1-carboxamide134

¹H NMR (400 MHz, DMSO-d₆) δ 13.38 (br s, 1H), 8.10 (d J = 1.3 Hz, 1H),7.88 (d J = 8.3 Hz, 1H), 7.74 (s, 1H), 7.51 (dd, J = 1.8, 8.4 Hz, 1H),5.18- 4.91 (m, 1H), 3.12 (s, 3H), 2.93 (s, 3H), 2.24 (br d, J = 2.1 Hz,1H), 2.21 (d, J = 2.8 Hz, 3H), 1.83- 1.67 (m, 1H), 1.31 (ddd, J = 2.8,6.3, 12.7 Hz, 1H); LCMS(electrospray) m/z 455.9 (M + H+). B6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)benzo[d]thiazol-6-yl)-N,N,5-trimethyl-1H-indazole-7-carboxamide 135

¹H NMR (400 MHz, DMSO-d₆) δ 13.50 (s, 1H), 12.85 (s, 1H), 8.21 (d, J =1.4 Hz, 1H), 8.04 (s, 2H), 7.92 (d, J = 8.4 Hz, 1H), 7.84 (s, 1H), 7.60(dd, J = 1.7, 8.3 Hz, 1H), 5.20-4.94 (m, 1H), 2.32- 2.18 (m, 1H),1.84-1.69 (m, 1H), 1.29~1.36(m, 1H); LCMS(electrospray) m/z 448.1 (M +H+). B 5-chloro-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)benzo[d]thiazol-6-yl)-1H- indazole-7-carboxamide 136

¹H NMR (400 MHz, DMSO-d₆) δ 13.12 (br s, 1H), 12.76 (br d, J = 12.7 Hz,1H), 8.00 (s, 1H), 7.85 (d, J = 8.3 Hz, 1H), 7.54 (s, 1H), 7.43 (dd, J =1.6, 8.2 Hz, 1H), 5.21-4.89 (m, 1H), 3.21 (q, J = 6.9 Hz, 2H), 2.94 (s,3H), 2.55 (br d, J = 7.6 Hz, 2H), 2.28- 2.19 (m, 1H), 1.83-1.68 (m, 1H),1.37-1.26 (m, 1H), 1.07 (dt, J = 4.0, 7.1 Hz, 6H); LCMS(electrospray)m/z 456.2 (M + H+). B (1S,2S)-N-(6-(5-ethyl-7-(ethyl(methyl)amino)-6-fluoro-1H- indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 137

¹H NMR (400 MHz, DMSO-d₆) δ 13.11 (s, 1H), 8.04 (d, J = 1.4 Hz, 1H),7.85 (d, J = 8.6 Hz, 1H), 7.64 (s, 1H), 7.47 (dd, J = 1.8, 8.3 Hz, 1H),5.19- 4.89 (m, 1H), 3.23-3.17 (m, 2H), 2.93 (d, J = 1.9 Hz, 3H),2.28-2.20 (m, 1H), 2.17 (d, J = 3.1 Hz, 3H), 1.85-1.68 (m, 1H),1.38-1.23 (m, 1H), 1.06 (t, J = 7.1 Hz, 3H); LCMS(electrospray) m/z441.14 (M + H+). B (1S,2S)-N-(6-(7-(ethyl(methyl)amino)-6-fluoro-5-methyl-1H-indazol-4- yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 138

¹H NMR (400 MHz, DMSO-d₆) δ 13.34 (br s, 1H), 8.04 (d, J = 1.3 Hz, 1H),7.83 (d, J = 8.2 Hz, 1H), 7.68 (s, 1H), 7.49 (dd, J = 1.7, 8.3 Hz, 1H),5.16- 4.94 (m, 1H), 3.23 (q, J = 7.1 Hz, 2H), 2.95 (d, J = 2.0 Hz, 3H),2.28-2.22 (m, 1H), 2.20 (s, 3H), 1.82- 1.68 (m, 1H), 1.31 (tdd, J = 6.2,8.9, 12.6 Hz, 1H), 1.07 (t, J = 7.1 Hz, 3H); LCMS(electrospray) m/z474.1 (M + H+). B (1S,2S)-N-(6-(7-(ethyl(methyl)amino)-6-fluoro-5-(methylthio)-1H-indazol-4- yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 139

¹H NMR (400 MHz, DMSO-d₆) δ 13.31 (s, 1H), 12.77 (s, 1H), 8.33 (s, 1H),8.24 (br s, 1H), 7.89- 7.81 (m, 1H), 7.80-7.74 (m, 1H), 7.13 (br d, J =13.7 Hz, 1H), 5.17-4.92 (m, 1H), 2.95 (br s, 6H), 2.27-2.18 (m, 1H),1.82-1.69 (m, 1H), 1.31 (br s, 1H); LCMS(electrospray) m/z 414.2 (M +H+). B (1S,2S)-N-(6-(7-(dimethylamino)-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 140

¹H NMR (400 MHz, DMSO-d₆) δ 14.04 (br s, 1H), 12.83 (br s, 1H),8.47-8.36 (m, 2H), 7.92-7.83 (m, 2H), 7.45 (br d, J = 11.7 Hz, 1H),5.19-4.95 (m, 1H), 2.30-2.20 (m, 1H), 1.84-1.70 (m, 1H), 1.34 (ddd, J =2.4, 6.2, 12.9 Hz, 1H); LCMS(electrospray) m/z 455.2 (M + H+). B(1S,2S)-2-fluoro-N-(6-(6-fluoro-7- (trifluoromethoxy)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)cyclopropane-1- carboxamide 141

¹H NMR (400 MHz, DMSO-d₆) δ 13.56 (s, 1 H) 12.81 (s, 1 H) 8.42 (s, 1 H)8.34 (s, 1 H) 7.89-7.82 (m, 2 H) 7.29 (d, J = 10.4 Hz, 1 H) 5.14-4.97(m, 1 H) 2.49 (s, 3 H) 2.28-2.23 (m, 1 H) 1.80-1.73 (m, 1 H) 1.35-1.30(m, 1 H); LCMS(electrospray) m/z 416.9 (M + H+). B(1S,2S)-2-fluoro-N-(6-(6-fluoro-7- (methylthio)-1H-indazol-4-yl)benzo[d]thiazol-2-yl)cyclopropane-1- carboxamide 142

¹H NMR (400 MHz, DMSO-d₆) δ 13.21-13.61 (m, 1 H) 12.76 (s, 1 H) 8.35 (d,J = 1.50 Hz, 1 H) 8.31 (s, 1 H) 7.85-7.89 (m, 1 H) 7.79 (dd, J = 8.38,1.75 Hz, 1 H) 7.34-7.39 (m, 1 H) 7.27-7.32 (m, 1 H) 4.93-5.17 (m, 1 H)3.17 (s, 1 H) 2.62 (s, 3 H) 2.20-2.29 (m, 1 H) 1.70-1.82 (m, 1 H) 1.32(ddt, J = 12.77, 8.93, 6.35, 6.35 Hz, 1 H); LCMS(electrospray) m/z 399.0(M + H+). B (1S,2S)-2-fluoro-N-(6-(7-(methylthio)-1H-indazol-4-yl)benzo[d]thiazol-2- yl)cyclopropane-1-carboxamide 143

¹H NMR (400 MHz, DMSO-d₆) δ 12.77 (br s, 1H), 8.15-7.99 (m, 2H), 7.83(br d, J = 8.3 Hz, 1H), 7.45 (br d, J = 8.1 Hz, 1H), 7.18 (br s, 1H),5.17- 4.93 (m, 1H), 2.33 (s, 3H), 2.25 (br s, 1H), 1.84- 1.70 (m, 1H),1.37-1.27 (m, 1H); LCMS(electrospray) m/z 346.1(M + H+). B(1S,2S)-N-(6-(5-chloro-7-cyano-6-fluoro-1H-indazol-4-yl)benzo[d]thiazol-2-yl)-2-fluorocyclopropane-1-carboxamide 144

¹H NMR (400 MHz, DMSO-d₆) δ 13.42 (br s, 1H), 12.82 (br s, 1H), 8.11 (s,1H), 7.98 (s, 1H), 7.85 (d, J = 8.3 Hz, 1H), 7.55 (td, J = 2.1, 8.3 Hz,1H), 7.47 (dd, J = 0.7, 9.7 Hz, 1H), 5.18-4.90 (m, 1H), 2.79 (s, 3H),2.63 (d, J = 1.0 Hz, 3H), 2.24 (td, J = 6.9, 13.6 Hz, 1H), 1.85-1.67 (m,1H), 1.39-1.25 (m, 1H); LCMS(electrospray) m/z 442.2 (M + H+). B6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)benzo[d]thiazol-6-yl)-N,N-dimethyl-1H-indazole-7-carboxamide 145

¹H NMR (400 MHz, DMSO-d₆) δ 13.42 (br s, 1H), 12.82 (br s, 1H), 8.11 (s,1H), 7.98 (s, 1H), 7.85 (d, J = 8.3 Hz, 1H), 7.55 (td, J = 2.1, 8.3 Hz,1H), 7.47 (dd, J = 0.7, 9.7 Hz, 1H), 5.18-4.90 (m, 1H), 2.79 (s, 3H),2.63 (d, J = 1.0 Hz, 3H), 2.24 (td, J = 6.9, 13.6 Hz, 1H), 1.85-1.67 (m,1H), 1.39-1.25 (m, 1H); LCMS(electrospray) m/z 442.2 (M + H+). B6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)benzo[d]thiazol-6-yl)-N,N-dimethyl-1H-indazole-5-carboxamide 146

¹H NMR (400 MHz, DMSO-d₆) δ 13.04 (s, 1H), 12.86 (s, 1H), 8.19 (d, J =8.8 Hz, 1H), 7.74 (s, 1H), 7.65 (d, J = 8.4 Hz, 1H), 7.48 (d, J = 8.4Hz, 1H), 7.29 (d, J = 8.4 Hz, 1H), 5.14-4.93 (m, 1H), 2.35 (s, 3H),2.29-2.20 (m, 1H), 1.77-1.70 (m, 1H), 1.35-1.26 (m, 1H); LCMS(electrospray) m/z 368.1 (M + H)+. D (1S,2S)-2-fluoro-N-(5-(5-methyl-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2- yl)cyclopropane-1-carboxamide 147

¹H NMR (400 MHz, DMSO-d₆) δ 12.96 (s, 1H), 8.25 (d, J = 8.0 Hz, 1H),7.80 (s, 1H), 7.71 (d, J = 8.4 Hz, 1H), 7.42 (d, J = 10.0 Hz, 1H),5.17-4.98 (m, 1H), 2.69 (s, 3H), 2.28-2.21 (m, 1H), 1.81-1.71 (m, 1H),1.37-1.28 (m, 1H); LCMS (electrospray) m/z 386.1 (M + H)+. D(1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2- yl)cyclopropane-1-carboxamide.3 HCl 148

¹H NMR (400 MHz, DMSO-d₆) δ 13.10 (br s, 1H), 12.95 (s, 1H), 8.21 (d, J= 8.0 Hz, 1H), 7.53 (d, J = 8.0 Hz, 1H), 7.37 (d, J = 10.1 Hz, 1H),5.18-4.97 (m, 1H), 2.27 (s, 3H), 2.16 (td, J = 6.9, 13.8 Hz, 1H),1.74-1.60 (m, 1H), 1.25-1.11 (m, 1H); LCMS (electrospray) m/z 432.1 (M +H)+. D (1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl-3-(methylthio)-1H-indazol-4- yl)thiazolo[5,4-b]pyridin-2-yl)cyclopropane-1-carboxamide. 3 HCl 149

¹H NMR (400 MHz, DMSO-d₆) δ 13.77 (s, 1H), 12.97 (s, 1H), 8.27 (d, J =8.4 Hz, 1H), 7.93 (s, 1H), 7.82 (d, J = 8.5 Hz, 1H), 5.20-4.95 (m, 1H),4.40 (q, J = 7.0 Hz, 2H), 2.31-2.23 (m, 1H), 1.85-1.71 (m, 1H), 1.41 (t,J = 6.9 Hz, 3H), 1.38-1.30 (m, 1H); LCMS (electrospray) m/z 450.2 (M +H)+. C (1S,2S)-N-(5-(5-chloro-7-ethoxy-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 150

¹H NMR (400 MHz, DMSO-d₆) δ 12.93 (s, 1 H), 8.25 (d, J = 8.31 Hz, 1 H),7.64-7.59 (m, 2 H), 7.39 (d, J = 11.62 Hz, 1 H), 5.19-4.96 (m, 1 H),3.08 (dt, J = 14.15, 7.17 Hz, 1 H), 2.30-2.23 (m, 1 H), 1.83- 1.71 (m, 1H), 1.40-1.32 (m, 1 H), 1.31-1.23 (m, 6 H); LCMS (electrospray) m/z414.2 (M + H)+. D (1S,2S)-2-fluoro-N-(5-(6-fluoro-5-isopropyl-1H-indazol-4-yl)thiazolo[5,4- b]pyridin-2-yl)cyclopropane-1-carboxamide. 2 TFA 151

¹H NMR (400 MHz, DMSO-d₆) δ 12.91 (s, 1 H), 8.25 (d, J = 8.56 Hz, 1 H),8.00 (s, 1 H), 7.95 (d, J = 8.44 Hz, 1 H), 7.40 (d, J = 10.88 Hz, 1 H),z, 1 H), 5.21-4.94 (m, 1 H), 2.30-2.23 (m, 1 H), 1.84- 1.69 (m, 1 H),1.41-1.28 (m, 1 H); LCMS (electrospray) m/z 387.2 (M + H)+. D(1S,2S)-N-(5-(5-amino-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 152

¹H NMR (400 MHz, DMSO-d₆) δ 13.18 (br s, 1H), 12.94 (br s, 1H), 8.26 (d,J = 8.2 Hz, 1H), 7.72 (s, 1H), 7.68 (d, J = 8.3 Hz, 1H), 7.42 (d, J =10.1 Hz, 1H), 5.20-4.95 (m, 1H), 2.65 (dq, J = 2.4, 7.2 Hz, 2H), 2.27(m, 1H), 1.85-1.69 (m, 1H), 1.34 (m, 1H), 1.11 (t, J = 7.0 Hz, 3H); LCMS(electrospray) m/z 400.4 (M + H)+. D (1S,2S)-N-(5-(5-ethyl-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 153

¹H NMR (400 MHz, DMSO-d₆) δ 12.99 (s, 1H), 8.29 (d, J = 8.4 Hz, 1H),7.91 (d, J = 0.9 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.71 (dd, J = 0.9,9.2 Hz, 1H), 5.20-4.96 (m, 1H), 2.31-2.23 (m, 1H), 1.84-1.71 (m, 1H),1.40-1.31 (m, 1H); LCMS (electrospray) m/z 406.3 (M + H)+. D(1S,2S)-N-(5-(5-chloro-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 154

¹H NMR (400 MHz, DMSO-d₆) δ 13.44 (br s, 1H), 12.96 (s, 1H), 8.26 (d, J= 8.3 Hz, 1H), 7.89 (s, 1H), 7.83 (d, J = 8.3 Hz, 1H), 5.21-4.95 (m,1H), 3.30 (q, J = 6.4 Hz, 4H), 2.31-2.22 (m, 1H), 1.84-1.71 (m, 1H),1.41-1.27 (m, 2H), 1.02 (t, J = 7.1 Hz, 6H); LCMS (electrospray) m/z477.3 (M + H)+. D (1S,2S)-N-(5-(5-chloro-7-(diethylamino)-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 155

¹H NMR (400 MHz, DMSO-d₆)) δ 12.93 (s, 1H), 8.25 (d, J = 8.6 Hz, 1H),8.16 (s, 1H), 7.98 (d, J = 8.4 Hz, 1H), 7.55 (d, J = 10.6 Hz, 1H),5.22-4.93 (m, 1H), 3.73 (s, 3H), 2.31-2.22 (m, 1H), 1.85-1.70 (m, 1H),1.41-1.28 (m, 1H); LCMS (electrospray) m/z 402.4 (M + H+). D(1S,2S)-2-fluoro-N-(5-(6-fluoro-5- methoxy-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)cyclopropane-1- carboxamide 156

¹H NMR (400 MHz, DMSO-d₆) δ 12.94 (s, 1H), 8.29-8.21 (m, 1H), 7.80 (d, J= 0.8 Hz, 1H), 7.74 (d, J = 8.4 Hz, 1H), 7.55 (dd, J = 0.8, 9.5 Hz, 1H),5.20-4.95 (m, 1H), 2.32-2.27 (m, 1H), 2.26 (s, 3H), 1.84-1.71 (m, 1H),1.35 (tdd, J = 6.4, 8.9, 13.0 Hz, 1H); LCMS(electrospray) m/z 418.3 (M +H+). D (1S,2S)-2-fluoro-N-(5-(6-fluoro-5-(methylthio)-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)cyclopropane-1- carboxamide 157

¹H NMR (400 MHz, DMSO-d₆) δ 13.84 (br s, 1H), 13.07 (s, 1H), 8.39-8.30(m, 2H), 8.08 (d, J = 8.4 Hz, 1H), 7.77 (d, J = 9.5 Hz, 1H), 5.21-4.97(m, 1H), 2.29 (td, J = 6.9, 13.4 Hz, 1H), 1.86-1.71 (m, 1H), 1.43-1.28(m, 1H); LCMS(electrospray) m/z 397.4 (M + H+). D(1S,2S)-N-(5-(5-cyano-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 158

¹H NMR (400 MHz, DMSO-d₆) δ 13.17 (br s, 1H), 12.83 (br s, 1H), 8.22 (d,J = 8.4 Hz, 1H), 7.87 (s, 1H), 7.81 (d, J = 8.4 Hz, 1H), 7.38 (d, J =10.2 Hz, 1H), 5.20-4.95 (m, 1H), 2.31-2.23 (m, 1H), 2.07- 1.98 (m, 1H),1.84-1.69 (m, 1H), 1.34 (tdd, J = 6.4, 8.9, 12.8 Hz, 1H), 0.72-0.61 (m,2H), 0.17- 0.06 (m, 2H); LCMS(electrospray) m/z 412.4 (M + H+). D(1S,2S)-N-(5-(5-cyclopropyl-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 159

¹H NMR (400 MHz, DMSO-d₆) δ 12.93 (s, 1H), 8.21 (d, J = 8.4 Hz, 1H),7.93 (br s, 1H), 7.78 (d, J = 8.5 Hz, 1H), 5.19-4.96 (m, 1H), 2.31-2.22(m, 1H), 1.84-1.70 (m, 1H), 1.39-1.27 (m, 1H), 1.22 (t, J = 7.1 Hz, 3H);LCMS(electrospray) m/z 449.3 (M + H+). D(1S,2S)-N-(5-(5-chloro-7-(ethylamino)-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 160

¹H NMR (400 MHz, DMSO-d₆) δ 13.46 (br s, 1H), 12.97 (s, 1H), 8.29 (d, J= 8.3 Hz, 1H), 7.83 (s, 1H), 7.78 (d, J = 8.4 Hz, 1H), 7.67 (d, J = 8.8Hz, 1H), 5.20-4.96 (m, 1H), 2.31-2.23 (m, 1H), 1.84-1.71 (m, 1H), 1.35(tdd, J = 6.4, 9.0, 13.0 Hz, 1H); LCMS(electrospray) m/z 452.0 (M + H+).D (1S,2S)-N-(5-(5-bromo-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 161

¹H NMR (400 MHz, DMSO-d₆) δ 12.91 (s, 1H), 8.23 (d, J = 8.4 Hz, 1H),7.72 (s, 1H), 7.64 (d, J = 8.4 Hz, 1H), 5.24-4.90 (m, 1H), 2.99 (s, 3H),2.98 (s, 3H), 2.70-2.58 (m, 2H), 2.31-2.21 (m, 1H), 1.86- 1.67 (m, 1H),1.41-1.26 (m, 1H), 1.12 (t, J = 7.4 Hz, 3H); LCMS(electrospray) m/z443.2 (M + H+). D (1S,2S)-N-(5-(7-(dimethylamino)-5-ethyl-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA 162

¹H NMR (400 MHz, DMSO-d₆) δ 13.47 (br s, 1H), 12.95 (s, 1H), 8.27 (d, J= 8.4 Hz, 1H), 7.79 (s, 1H), 7.69 (d J = 8.3 Hz, 1H), 5.18-4.96 (m, 1H),2.67- 2.64 (m, 2H), 2.53 (br s, 3H), 2.30-2.22 (m, 1H), 1.82-1.71 (m,1H), 1.35 (tdd, J = 6.5, 8.8, 12.9 Hz, 1H), 1.12 (t, J = 7.4 Hz, 3H);LCMS(electrospray) m/z 446.3 (M + H+). D(1S,2S)-N-(5-(5-ethyl-6-fluoro-7-(methylthio)-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA 163

¹H NMR (400 MHz, CHLOROFORM-d) δ 13.46 (br s, 1H), 12.98 (s, 1H), 8.27(d, J = 8.4 Hz, 1H), 7.88 (s, 1H), 7.73 (d, J = 8.4 Hz, 1H), 5.24-4.95(m, 1H), 3.51 (br t, J = 6.9 Hz, 3H), 3.03 (br t, J = 6.6 Hz, 2H), 2.28(br d, J = 2.6 Hz, 4H), 1.84-1.71 (m, 1H), 1.80-1.30 (m, 1H), 1.41-1.30(m, 1H); LCMS(electrospray) m/z 462.1 (M + H+). D(1S,2S)-2-fluoro-N-(5-(6-fluoro-7-((2-hydroxyethyl)thio)-5-methyl-1H-indazol- 4-yl)thiazolo[5,4-b]pyridin-2-yl)cyclopropane-1-carboxamide. 2TFA 164

¹H NMR (400 MHz, DMSO-d₆) δ 13.65 (br s, 1H), 13.02 (s, 1H), 8.30 (d, J= 8.4 Hz, 1H), 8.10 (s, 1H), 7.92 (d, J = 8.4 Hz, 1H), 7.67 (d, J = 11.2Hz, 1H), 5.19-4.97 (m, 1H), 3.18 (d, J = 1.0 Hz, 3H), 2.31- 2.25 (m,1H), 1.84-1.71 (m, 1H), 1.41-1.29 (m, 1H); LCMS(electrospray) m/z 434(M + H+). D (1S,2S)-2-fluoro-N-(5-(6-fluoro-5-(methylsulfinyl)-1H-indazol-4- yl)thiazolo[5,4-b]pyridin-2-yl)cyclopropane-1-carboxamide. 2 TFA 165

¹H NMR (400 MHz, DMSO-d₆) δ 13.52 (br s, 1H), 13.33 (br s, 1H), 12.97(s, 1H), 8.28 (d, J = 8.4 Hz, 1H), 8.09 (s, 1H), 7.81 (s, 1H), 7.71 (brs, 1H), 7.68 (d, J = 8.4 Hz, 1H), 5.25-4.96 (m, 1H), 3.97 (q, J = 7.1Hz, 2H), 3.93-3.87 (m, 1H), 3.78 (s, 2H), 3.70 (s, 1H), 2.72-2.62 (m,3H), 2.32-2.23 (m, 1H), 1.84-1.71 (m, 1H), 1.41-1.31 (m, 1H), 1.21 (t, J= 7.5 Hz, 1H), 1.12 (t, J = 7.4 Hz, 3H), 1.01 (t, J = 7.1 Hz, 3H), 0.94(t, J = 7.1 Hz, 1H); LCMS(electrospray) m/z 518.3 (M + H+). D ethyl2-((5-ethyl-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)thiazolo[5,4-b]pyridin-5-yl)- 1H-indazol-7-yl)thio)acetate.2 TFA 166

¹H NMR (400 MHz, DMSO-d₆) δ 13.48 (s, 1H), 8.10 (d, J = 8.2 Hz, 1H),7.81 (s, 1H), 7.58 (d, J = 8.2 Hz, 1H), 5.19-4.84 (m, 1H), 3.97 (s, 2H),3.02 (s, 3H), 2.91-2.76 (m, 6H), 2.74-2.62 (m, 2H), 2.21-2.10 (m, 1H),1.81-1.64(m, 1H), 1.29-1.19 (m, 1H), 1.13 (t, J = 7.3 Hz, 3H);LCMS(electrospray) m/z 517.1 (M + H+). D(1S,2S)-N-(5-(7-((2-(dimethylamino)-2-oxoethyl)thio)-5-ethyl-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 167

¹H NMR (400 MHz, DMSO-d₆) δ 7.82 (d, J = 7.9 Hz, 1H), 7.72 (s, 1H), 7.41(d, J = 8.2 Hz, 1H), 5.03- 4.68 (m, 1H), 3.18 (s, 1H), 2.86 (s, 1H),2.70- 2.63 (m, 2H), 2.01-1.91 (m, 1H), 1.72-1.57 (m, 1H), 1.12 (t, J =7.3 Hz, 3H), 1.05-0.96 (m, 1H); LCMS(electrospray) m/z 503.3 (M + H+). D(1S,2S)-N-(5-(5-ethyl-6-fluoro-7-((2- (methylamino)-2-oxoethyl)thio)-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 168

¹H NMR (400 MHz, DMSO-d₆) δ 7.82 (d, J = 7.9 Hz, 1H), 7.72 (s, 1H), 7.41(d, J = 8.2 Hz, 1H), 5.03- 4.68 (m, 1H), 3.18 (s, 1H), 2.86 (s, 1H),2.70- 2.63 (m, 2H), 2.01-1.91 (m, 1H), 1.72-1.57 (m, 1H), 1.12 (t, J =7.3 Hz, 3H), 1.05-0.96 (m, 1H); LCMS(electrospray) m/z 490.3 (M + H+). D2-((5-ethyl-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)thiazolo[5,4-b]pyridin-5-yl)- 1H-indazol-7-yl)thio)aceticacid 169

¹H NMR (400 MHz, CHLOROFORM-d) δ 8.15 (d, J = 8.3 Hz, 1H), 7.89 (br s,1H), 7.60 (d, J = 8.3 Hz, 1H), 5.10-4.76 (m, 1H), 3.13 (d, J = 1.6 Hz,6H), 2.35 (d, J = 3.4 Hz, 3H), 2.12-2.01 (m, 2H), 1.49- 1.33 (m, 1H);LCMS(electrospray) m/z429.1 (M + H+). D(1S,2S)-N-(5-(7-(dimethylamino)-6- fluoro-5-methyl-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 2TFA 170

¹H NMR (400 MHz, DMSO-d₆) δ 13.65 (s, 1H), 12.94 (br s, 1H), 8.25 (d, J= 8.4 Hz, 1H), 7.89- 7.84 (m, 1H), 7.75 (d, J = 8.3 Hz, 1H), 5.20-4.94(m, 1H), 2.56 (s, 3H), 2.28 (s, 3H), 2.27-2.23 (m, 1H), 1.84-1.72 (m,1H), 1.41-1.30 (m, 1H); LCMS(electrospray) m/z 464.0 (M + H+). D(1S,2S)-2-fluoro-N-(5-(6-fluoro-5,7- bis(methylthio)-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2- yl)cyclopropane-1-carboxamide. 2 TFA 171

¹H NMR (400 MHz, DMSO-d₆) δ 13.96 (s, 1H), 12.92 (s, 1H), 8.41 (d, J =6.5 Hz, 1H), 8.38 (d, J = 1.2 Hz, 1H), 8.29 (d, J = 8.6 Hz, 1H), 8.15(d, J = 7.7 Hz, 1H), 5.21-4.94 (m, 1H), 2.24 (s, 1H), 1.88- 1.69 (m,1H), 1.41-1.29 (m, 1H); LCMS(electrospray) m/z 0.887, 440.1 (M + H+). D(1S,2S)-2-fluoro-N-(5-(5-fluoro-6- (trifluoromethyl)-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2- yl)cyclopropane-1-carboxamide. TFA 172

¹H NMR (400 MHz, DMSO-d₆) δ 13.56-13.42 (m, 1H), 8.24 (d, J = 8.4 Hz,1H), 7.90 (br s, 1H), 7.79 (d, J = 8.4 Hz, 1H), 5.20-4.95 (m, 1H), 3.02(br d, J = 1.7 Hz, 6H), 2.27 (ddd, J = 2.0, 4.6, 6.7 Hz, 1H), 1.85-1.71(m, 1H), 1.38-1.30 (m, 1H), 1.30 (s, 1H); LCMS(electrospray) m/z 449.1(M + H+). D (1S,2S)-N-(5-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 173

¹H NMR (400 MHz, DMSO-d₆) δ 13.57-13.32 (m, 1H), 8.25 (dd, J = 3.0, 8.3Hz, 1H), 7.86 (br s, 1H), 7.70 (dd, J = 2.9, 8.3 Hz, 1H), 5.22-4.91 (m,1H), 2.53 (br s, 3H), 2.27 (br s, 3H), 1.83-1.70 (m, 1H), 1.40-1.27 (m,1H), 1.21 (br d, J = 10.5 Hz, 2H); LCMS(electrospray) m/z 431.07 (M +H+). D (1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl-7-(methylthio)-1H-indazol-4- yl)thiazolo[5,4-b]pyridin-2-yl)cyclopropane-1-carboxamide. 2 TFA 174

¹H NMR (400 MHz, DMSO-d₆) δ 13.76 (s, 1H), 12.98 (s, 1H), 8.29 (d, J =8.4 Hz, 1H), 7.98 (d, J = 1.3 Hz, 1H), 7.85 (d, J = 8.4 Hz, 1H),5.21-4.96 (m, 1H), 2.58 (s, 3H), 2.31-2.25 (m, 1H), 1.84- 1.72 (m, 1H),1.37-1.30 (m, 1H); LCMS(electrospray) m/z 452 (M + H+). D(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(methylthio)-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 175

¹H NMR (400 MHz, DMSO-d₆) δ 13.54-13.33 (m, 1H), 12.92 (s, 1H), 8.23 (d,J = 8.3 Hz, 1H), 7.82 (s, 1H), 7.68 (d, J = 8.3 Hz, 1H), 5.19-4.96 (m,1H), 4.33 (q, J = 7.0 Hz, 2H), 2.30-2.25 (m, 4H), 1.83-1.72 (m, 1H),1.39 (t, J = 7.0 Hz, 3H), 1.36-1.32 (m, 1H); LCMS(electrospray) m/z430.2 (M + H+). D (1S,2S)-N-(5-(7-ethoxy-6-fluoro-5-methyl-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 1 TFA 176

¹H NMR (400 MHz, DMSO-d₆) δ 13.90-13.81 (m, 1H), 12.94 (br s, 1H), 8.26(d, J = 8.4 Hz, 1H), 7.87-7.80 (m, 1H), 7.67 (d, J = 8.3 Hz, 1H), 5.17-4.95 (m, 1H), 2.76-2.68 (m, 2H), 2.27-2.19 (m, 1H), 1.82-1.73 (m, 1H),1.57-1.42 (m, 1H), 1.15- 1.11 (m, 3H); LCMS(electrospray) m/z 418 (M +H+). D (1S,2S)-N-(5-(5-ethyl-6,7-difluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 177

¹H NMR (400 MHz, DMSO-d₆) δ 13.36 (s, 1H), 12.97 (s, 1H), 8.29 (d, J =8.3 Hz, 1H), 7.92 (s, 1H), 7.74 (d, J = 8.3 Hz, 1H), 5.20-4.96 (m, 1H),3.14 (s, 3H), 2.31-2.23 (m, 4H), 1.84-1.71 (m, 1H), 1.35 (tdd, J = 6.4,8.9, 13.0 Hz, 1H); LCMS(electrospray) m/z 447.9 (M + H+). D(1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl-7-(methylsulfinyl)-1H-indazol-4- yl)thiazolo[5,4-b]pyridin-2-yl)cyclopropane-1-carboxamide. 1 TFA 178

¹H NMR (400 MHz, DMSO-d₆) δ 13.47 (s, 1H), 12.93 (s, 1H), 8.25 (d, J =8.0 Hz, 1H), 7.76 (s, 1H), 7.67-7.65 (m, 1H), 5.21-4.96 (m, 1H),4.37-4.31 (m, 2H), 2.68-2.64 (m, 2H), 2.34-2.33 (m, 1H), 1.81-1.68 (m,1H), 1.40 (t, J = 6.8 Hz, 3H), 1.19- 1.15 (m, 1H), 1.13 (t, J = 7.6 Hz,3H); LCMS(electrospray) m/z 444.2 (M + H+). D(1S,2S)-N-(5-(7-ethoxy-5-ethyl-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 1 TFA 179

¹H NMR (400 MHz, DMSO-d₆) δ 13.27 (br s, 1H), 12.97 (s, 1H), 10.16 (s,1H), 8.29 (d, J = 8.4 Hz, 1H), 7.91 (s, 1H), 7.85 (d, J = 8.3 Hz, 1H),5.18- 4.98 (m, 1H), 2.28 (ddd, J = 2.4, 4.3, 6.6 Hz, 1H), 2.19 (s, 3H),1.82-1.73 (m, 1H), 1.35 (ddd, J = 2.6, 6.3, 12.9 Hz, 1H);LCMS(electrospray) m/z 463.1(M + H+). D(1S,2S)-N-(5-(7-acetamido-5-chloro-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 1 TFA 180

¹H NMR (400 MHz, DMSO-d₆) δ 13.68 (br s, 1H), 13.02 (s, 1H), 8.32 (d, J= 8.4 Hz, 1H), 8.05 (br s, 1H), 7.87 (d, J = 8.4 Hz, 1H), 5.20-4.98 (m,1H), 3.19 (s, 3H), 2.31-2.25 (m, 1H), 1.85-1.71 (m, 1H), 1.36 (tdd, J =6.6, 8.8, 13.0 Hz, 1H); LCMS(electrospray) m/z 468 (M + H+). D(1S,2S)-N-(5-(5-chloro-6-fluoro-7- (methylsulfinyl)-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 181

¹H NMR (400 MHz, DMSO-d₆) δ 12.96-12.91 (m, 2H), 9.96 (s, 1H), 8.26 (d,J = 8.4 Hz, 1H), 7.79 (s, 1H), 7.71 (d, J = 8.3 Hz, 1H), 5.20-4.94 (m,1H), 2.27 (d, J = 2.9 Hz, 3H), 2.17 (s, 4H), 1.84- 1.71 (m, 1H),1.42-1.30 (m, 1H); LCMS(electrospray) m/z 442.10 (M + H+). D(1S,2S)-N-(5-(7-acetamido-6-fluoro-5-methyl-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 1 TFA 182

¹H NMR (400 MHz, DMSO-d₆) δ 13.19 (s, 1H), 12.99 (s, 1H), 8.31 (d, J =8.4 Hz, 1H), 7.97 (s, 1H), 7.76 (d, J = 8.3 Hz, 1H), 5.21-4.95 (m, 1H),3.51 (s, 3H), 2.33-2.25 (m, 4H), 1.85-1.71 (m, 1H), 1.41-1.28 (m, 1H);LCMS(electrospray) m/z 463.06 (M + H+). D(1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl-7-(methylsulfonyl)-1H-indazol-4- yl)thiazolo[5,4-b]pyridin-2-yl)cyclopropane-1-carboxamide. 1 TFA 183

¹H NMR (400 MHz, DMSO-d₆) δ 13.44-13.24 (m, 1H), 12.99 (s, 1H), 8.30 (d,J = 8.3 Hz, 1H), 7.98-7.86 (m, 1H), 7.76 (d, J = 8.4 Hz, 1H), 5.27- 4.90(m, 1H), 3.99 (s, 3H), 2.31-2.24 (m, 4H), 1.82-1.70 (m, 1H), 1.44-1.27(m, 1H); LCMS(electrospray) m/z 444.0 (M + H+). D methyl6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)thiazolo[5,4-b]pyridin-5-yl)-5-methyl-1H-indazole-7-carboxylate. 1 TFA 184

¹H NMR (400 MHz, DMSO-d₆) δ 13.83-13.51 (m, 1H), 12.93 (s, 1H), 8.23 (d,J = 8.4 Hz, 1H), 7.84 (s, 1H), 7.73 (d, J = 8.4 Hz, 1H), 5.22-4.93 (m,1H), 4.51-4.26 (m, 2H), 2.30-2.28 (m, 1H), 2.06-2.03 (m, 1H), 1.86-1.73(m, 1H), 1.64-1.52 (m, 1H), 1.42 (t, J = 7.0 Hz, 3H), 1.33 (m, J = 6.7,14.0 Hz, 1H); LCMS(electrospray) m/z 462.2 (M + H+). D(1S,2S)-N-(5-(7-ethoxy-6-fluoro-5-(methylthio)-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 1 TFA 185

¹H NMR (400 MHz, DMSO-d₆) δ 13.48 (s, 1H), 13.03 (s, 1H), 8.34 (d, J =8.3 Hz, 1H), 8.09 (d, J = 1.3 Hz, 1H), 7.89 (d, J = 8.3 Hz, 1H),5.20-4.98 (m, 1H), 3.57 (s, 3H), 2.31-2.25 (m, 1H), 1.85- 1.73 (m, 1H),1.41-1.31 (m, 1H); LCMS(electrospray) m/z 484 (M + H+). D(1S,2S)-N-(5-(5-chloro-6-fluoro-7- (methylsulfonyl)-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 1TFA 186

¹H NMR (400 MHz, DMSO-d₆) δ 13.92-13.91 (m, 1H), 13.91-13.90 (m, 1H),13.86 (br s, 1H), 8.23 (d, J = 8.3 Hz, 1H), 7.93 (br d, J = 2.7 Hz, 1H),7.68 (d, J = 8.3 Hz, 1H), 5.17-4.95 (m, 1H), 2.32- 2.31 (m, 1H), 2.31(d, J = 2.9 Hz, 2H), 2.26 (dt, J = 2.2, 4.5 Hz, 1H), 1.84-1.73 (m, 1H),1.32-1.25 (m, 1H); LCMS(electrospray) m/z 404.2 (M + H+). D(1S,2S)-N-(5-(6,7-difluoro-5-methyl-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 1 TFA 187

¹H NMR (400 MHz, DMSO-d₆) δ 8.42 (d, J = 8.3 Hz, 1H), 8.14 (d, J = 3.2Hz, 1H), 7.91 (d, J = 8.4 Hz, 1H), 5.38-5.15 (m, 1H), 2.71-2.70 (m, 3H),2.45 (br s, 1H), 2.03-1.89 (m, 1H), 1.41 (s, 1H); LCMS(electrospray) m/z436.1 (M + H+). D (1S,2S)-N-(5-(6,7-difluoro-5-(methylthio)-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 188

¹H NMR (400 MHz, METHANOL-d₄) δ 8.25 (d, J = 8.4 Hz, 1H), 7.84 (s, 1H),7.71 (d, J = 8.3 Hz, 1H), 5.04 (dt, J = 3.9, 6.2 Hz, 1H), 2.32 (d, J =3.3 Hz, 3H), 2.24-2.16 (m, 1H), 1.98-1.84 (m, 1H), 1.34-1.29 (m, 1H);LCMS(electrospray) m/z 429.9 (M + H+). D 6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1- carboxamido)thiazolo[5,4-b]pyridin-5-yl)-5-methyl-1H-indazole-7-carboxylic acid. 1 TFA 189

¹H NMR (400 MHz, DMSO-d₆) δ 14.34 (s, 1H), 8.31-8.28 (m, 1H), 8.05 (s,1H), 7.88 (d, J = 8.4 Hz, 1H), 5.17-4.98 (m, 1H), 3.25 (s, 3H), 2.28(ddd, J = 1.8, 4.7, 6.8 Hz, 1H), 1.83 (s, 3H), 1.75 (dt, J = 3.8, 6.9Hz, 1H), 1.38-1.32 (m, 1H); LCMS(electrospray) m/z 477.0 (M + H+). D(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(N- methylacetamido)-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 190

¹H NMR (400 MHz, DMSO-d₆) δ 13.61 (br s, 1H), 12.99-12.91 (m, 1H),8.31-8.24 (m, 1H), 7.94- 7.88 (m, 1H), 7.77-7.70 (m, 1H), 5.23-4.96 (m,1H), 3.22 (s, 3H), 2.30 (d, J = 2.8 Hz, 3H), 2.28- 2.23 (m, 1H), 1.80(s, 3H), 1.77-1.70 (m, 1H), 1.41-1.29 (m, 1H); LCMS(electrospray) m/z456.12 (M + H+). D (1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl-7-(N-methylacetamido)-1H-indazol-4- yl)thiazolo[5,4-b]pyridin-2-yl)cyclopropane-1-carboxamide. 1 TFA 191

¹H NMR (400 MHz, DMSO-d₆) δ 12.90 (br, 2H), 8.20 (d, J = 8.0 Hz, 1H),7.83 (s, 1H), 7.76 (d, J = 8.4 Hz, 1H), 7.49 (s, 1H), 5.15-4.98 (m, 1H),5.04 (d, J = 5.2 Hz, 1H), 3.24 (s, 3H), 2.32-2.26 (m, 2H), 1.80-1.73 (m,1H), 1.35-1.23 (m, 1H); LCMS (electrospray) m/z 450.1 (M + H)+. D(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(2- methylhydrazineyl)-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 192

¹H NMR (400 MHz, DMSO-d₆) δ 12.94 (s, 1H), 12.88 (s, 1H), 8.37 (s, 1H),8.22 (d, J = 8.4 Hz, 1H), 7.90 (s, 1H), 7.77 (d, J = 8.4 Hz, 1H),5.15-4.98 (m, 1H), 2.60 (d, J = 5.2 Hz, 3H), 2.18-2.13 (m, 1H),1.71-1.63 (m, 1H), 1.35-1.12 (m, 10H); LCMS (electrospray) m/z 550.1(M + H)+. D tert-butyl 2-(5-chloro-6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1-carboxamido)thiazolo[5,4-b]pyridin-5-yl)-1H-indazol-7-yl)-1-methylhydrazine-1- carboxylate 193

¹H NMR (400 MHz, DMSO-d₆) δ 13.87-13.62 (m, 1H), 8.29 (d, J = 8.5 Hz,1H), 7.98 (s, 1H), 7.86 (d, J = 8.5 Hz, 1H), 5.18-4.95 (m, 1H), 3.12 (s,3H), 2.93 (s, 3H), 2.27 (ddd, J = 2.0, 4.6, 6.7 Hz, 1H), 1.82-1.71 (m,1H), 1.34 (ddd, J = 2.6, 6.3, 13.0 Hz, 1H); LCMS(electrospray) m/z 476.9(M + H+). D 5-chloro-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)thiazolo[5,4-b]pyridin-5-yl)-N,N-dimethyl-1H-indazole-7-carboxamide 194

¹H NMR (400 MHz, DMSO-d₆) δ 13.36 (br s, 1H), 12.90 (br s, 1H), 8.21 (d,J = 8.8 Hz, 1H), 7.77 (s, 1H), 7.70 (d, J = 8.4 Hz, 1H), 5.19-4.95 (m,1H), 2.99 (s, 6H), 2.27 (s, 4H), 1.84-1.70 (m, 1H), 1.40- 1.28 (m, 1H);LCMS(electrospray) m/z 461 (M + H+). D(1S,2S)-N-(5-(7-(dimethylamino)-6- fluoro-5-(methylthio)-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 195

¹H NMR (400 MHz, DMSO-d₆) δ 8.65 (br d, J = 3.3 Hz, 1H), 8.19-8.12 (m,1H), 7.95 (s, 1H), 7.77 (d, J = 8.3 Hz, 1H), 5.17-4.89 (m, 1H), 2.91 (d,J = 4.5 Hz, 3H), 2.23-2.14 (m, 1H), 1.85-1.63 (m, 1H), 1.35-1.17 (m,1H); LCMS(electrospray) m/z 462.9 (M + H+). D5-chloro-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)thiazolo[5,4-b]pyridin-5-yl)-N-methyl-1H-indazole-7-carboxamide 196

¹H NMR (400 MHz, DMSO-d₆) δ 13.53-13.38 (m, 1H), 13.59-13.37 (m, 1H),8.31-8.23 (m, 1H), 7.96-7.87 (m, 1H), 7.85-7.76 (m, 1H), 5.21- 4.96 (m,1H), 3.31 (br s, 2H), 3.09-2.92 (m, 3H), 2.35-2.23 (m, 1H), 1.87-1.72(m, 1H), 1.42-1.30 (m, 1H), 1.14-1.05 (m, 3H); LCMS(electrospray) m/z463.7 (M + H+). D (1S,2S)-N-(5-(5-chloro-7-(ethyl(methyl)amino)-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 197

¹H NMR (400 MHz, DMSO-d₆) δ 13.48-13.33 (m, 1H), 8.24 (d, J = 8.4 Hz,1H), 7.86 (s, 1H), 7.72 (d, J = 8.4 Hz, 1H), 5.19-4.93 (m, 1H), 3.12 (s,3H), 2.92 (s, 3H), 2.28 (d, J = 2.9 Hz, 3H), 2.27- 2.22 (m, 1H),1.82-1.69 (m, 1H), 1.39-1.28 (m, 1H); LCMS(electrospray) m/z 457.1 (M +H+). D 6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)thiazolo[5,4-b]pyridin-5-yl)- N,N,5-trimethyl-1H-indazole-7-carboxamide 198

¹H NMR (400 MHz, DMSO-d₆) δ 8.35 (s, 1H), 8.22 (d, J = 8.4 Hz, 1H), 7.96(s, 1H), 7.65 (d, J = 8.4 Hz, 1H), 5.17-4.91 (m, 1H), 2.30-2.19 (m, 1H),1.83-1.69 (m, 1H), 1.39-1.28 (m, 1H); LCMS(electrospray) m/z 474.1 (M +H+). D (1S,2S)-N-(5-(7-chloro-6-fluoro-5-(trifluoromethyl)-1H-indazol-4- yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 199

¹H NMR (400 MHz, DMSO-d₆) δ 13.01-12.83 (m, 1H), 8.30-8.14 (m, 1H),7.98-7.94 (m, 1H), 7.80 (s, 1H), 7.71-7.59 (m, 1H), 5.28-4.88 (m, 1H),2.49-2.48 (m, 3H), 2.27-2.24 (m, 4H), 1.83- 1.72 (m, 1H), 1.39-1.30 (m,1H); LCMS(electrospray) m/z 400.0 (M + H+). D(1S,2S)-2-fluoro-N-(5-(6-fluoro-5,7-dimethyl-1H-indazol-4-yl)thiazolo[5,4- b]pyridin-2-yl)cyclopropane-1-carboxamide. 1 TFA 200

¹H NMR (400 MHz, DMSO-d₆) δ 13.15 (s, 1H), 13.03-12.78 (m, 1H), 8.23 (d,J = 8.4 Hz, 1H), 7.74-7.61 (m, 2H), 5.20-4.94 (m, 1H), 3.23 (br d, J =7.1 Hz, 2H), 2.95 (d, J = 1.8 Hz, 3H), 2.63 (br d, J = 5.8 Hz, 2H),2.29-2.24 (m, 1H), 1.83- 1.71 (m, 1H), 1.40-1.29 (m, 1H), 1.12 (t, J =7.4 Hz, 3H), 1.06 (t, J = 7.1 Hz, 3H); LCMS(electrospray) m/z 457.0 (M +H+). D (1S,2S)-N-(5-(5-ethyl-7- (ethyl(methyl)amino)-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 201

¹H NMR (400 MHz, DMSO-d₆) δ 13.19 (br s, 1H), 12.89 (br s, 1H), 8.24 (d,J = 8.5 Hz, 1H), 8.15 (s, 1H), 8.01 (d, J = 8.5 Hz, 1H), 7.53 (d, J =10.5 Hz, 1H), 5.19-4.96 (m, 1H), 3.91 (q, J = 7.0 Hz, 2H), 2.31-2.23 (m,1H), 1.84-1.72 (m, 1H), 1.39-1.30 (m, 1H), 1.15 (t, J = 6.9 Hz, 3H);LCMS(electrospray) m/z 416.0 (M + H+). D(1S,2S)-N-(5-(5-ethoxy-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 202

¹H NMR (400 MHz, DMSO-d₆) δ 13.20-13.00 (m, 1H), 12.95-12.86 (m, 1H),8.23 (d, J = 8.3 Hz, 1H), 7.80 (s, 1H), 7.67 (d, J = 8.4 Hz, 1H), 6.98-6.89 (m, 1H), 5.21-4.94 (m, 1H), 4.09 (br t, J = 5.9 Hz, 2H), 3.38-3.33(m, 2H), 3.04-2.98 (m, 3H), 2.57-2.52 (m, 3H), 2.28 (br dd, J = 2.1, 4.4Hz, 1H), 2.26-2.26 (m, 1H), 2.25 (d, J = 3.1 Hz, 3H), 1.83-1.71 (m, 1H),1.39-1.30 (m, 1H); LCMS(electrospray) m/z 516.1 (M + H+). D2-((6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)thiazolo[5,4-b]pyridin-5-yl)- 5-methyl-1H-indazol-7-yl)(methyl)amino)ethyl methylcarbamate 203

¹H NMR (400 MHz, DMSO-d₆) δ 13.13 (s, 1H), 8.23 (d, J = 8.3 Hz, 1H),7.77 (s, 1H), 7.68 (d, J = 8.3 Hz, 1H), 5.23-4.94 (m, 1H), 3.22 (q, J =6.9 Hz, 2H), 2.95 (d, J = 2.1 Hz, 3H), 2.30-2.27 (m, 1H), 2.25 (d, J =3.2 Hz, 3H), 1.87-1.68 (m, 1H), 1.35 (tdd, J = 6.5, 8.7, 13.1 Hz, 1H),1.06 (t, J = 7.2 Hz, 3H); LCMS(electrospray) m/z 442.14 (M + H+). D(1S,2S)-N-(5-(7-(ethyl(methyl)amino)-6- fluoro-5-methyl-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 204

¹H NMR (400 MHz, DMSO-d₆) δ 13.27-13.06 (m, 1H), 8.21 (br d, J = 8.1 Hz,1H), 7.78 (br s, 1H), 7.66 (br d, J = 8.4 Hz, 1H), 5.19-4.95 (m, 1H),4.91 (br s, 1H), 3.65-3.55 (m, 2H), 3.27-3.14 (m, 2H), 3.04-2.94 (m,3H), 2.28-2.19 (m, 4H), 1.82- 1.68 (m, 1H), 1.38-1.26 (m, 1H);LCMS(electrospray) m/z 459.1 (M + H+). D(1S,2S)-2-fluoro-N-(5-(6-fluoro-7-((2-hydroxyethyl)(methyl)amino)-5-methyl-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2- yl)cyclopropane-1-carboxamide205

¹H NMR (400 MHz, DMSO-d₆) δ 13.63 (br s, 1H), 8.27 (d, J = 8.3 Hz, 1H),7.99 (s, 1H), 7.74 (d, J = 8.3 Hz, 1H), 5.19-4.95 (m, 1H), 2.29 (d, J =2.9 Hz, 3H), 2.28-2.22 (m, 1H), 1.84-1.70 (m, 1H), 1.39- 1.27 (m, 1H);LCMS(electrospray) m/z 454.2 (M + H+). D(1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl-7-(trifluoromethyl)-1H-indazol-4- yl)thiazolo[5,4-b]pyridin-2-yl)cyclopropane-1-carboxamide 206

¹H NMR (400 MHz, DMSO-d₆) δ 13.24 (br d, J = 2.9 Hz, 1H), 8.50-8.44 (m,1H), 8.18 (d, J = 8.3 Hz, 1H), 7.84 (s, 1H), 7.67 (d, J = 8.2 Hz, 1H),5.17- 4.89 (m, 1H), 2.91 (d, J = 4.4 Hz, 3H), 2.29 (d, J = 2.8 Hz, 3H),2.24-2.18 (m, 1H), 1.83-1.67 (m, 1H), 1.35-1.21 (m, 1H);LCMS(electrospray) m/z 442.10 (M + H+). D 6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1- carboxamido)thiazolo[5,4-b]pyridin-5-yl)-N,5-dimethyl-1H-indazole-7-carboxamide 207

¹H NMR (400 MHz, DMSO-d₆) δ 13.86-13.56 (m, 1H), 12.95 (s, 1H), 8.24 (d,J = 8.3 Hz, 1H), 7.73 (s, 1H), 7.62 (d, J = 8.3 Hz, 1H), 5.19-4.96 (m,1H), 3.03 (d, J = 2.2 Hz, 6H), 2.32-2.21 (m, 1H), 1.83-1.71 (m, 1H),1.41-1.31 (m, 1H); LCMS(electrospray) m/z 483.2 (M + H+). D(1S,2S)-N-(5-(7-(dimethylamino)-6-fluoro-5-(trifluoromethyl)-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 1TFA 208

¹H NMR (400 MHz, METHANOL-d₄) δ 8.23 (d, J = 8.4 Hz, 1H), 7.98 (d, J =3.3 Hz, 1H), 7.82 (d, J = 8.4 Hz, 1H), 5.04 (dt, J = 3.9, 6.2 Hz, 1H),2.20 (dtd, J = 4.3, 6.9, 9.1 Hz, 1H), 1.95-1.84 (m, 1H), 1.37-1.29 (m,1H); LCMS(electrospray) m/z 424.1 (M + H+). D(1S,2S)-N-(5-(5-chloro-6,7-difluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 2,2,2-trifluoroacetate. 1 TFA 209

¹H NMR (400 MHz, DMSO-d₆) δ 1.27-1.40 (m, 1 H), 1.71-1.83 (m, 1 H), 2.27(br s, 1 H), 4.95-5.19 (m, 1 H), 7.51 (s, 1 H), 7.65 (s, 1 H), 7.78 (brs, 1 H), 7.87 (br d, J = 8.68 Hz, 1 H), 8.05 (br s, 1 H), 8.21-8.38 (m,1 H), 12.77-13.42 (m, 1 H), 13.77- 14.05 (m, 1 H); LCMS(electrospray)m/z 456.1 (M + H+). D (1S,2S)-N-(5-(5-chloro-7-(difluoromethyl)-6-fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 210

¹H NMR (400 MHz, DMSO-d₆) δ 1.12 (br t, J = 7.40 Hz, 3 H), 1.27-1.42 (m,1 H), 1.68-1.85 (m, 1 H), 2.22-2.31 (m, 1 H), 2.68 (br d, J = 7.28 Hz, 2H), 4.90-5.23 (m, 1 H), 7.73 (d, J = 8.41 Hz, 1 H), 7.93 (br s, 1 H),8.30 (d, J = 8.28 Hz, 1 H), 12.60-13.33 (m, 1 H), 13.48-13.91 (m, 1 H);LCMS(electrospray) m/z 468.2 (M + H+). D(1S,2S)-N-(5-(5-ethyl-6-fluoro-7- (trifluoromethyl)-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 211

¹H NMR (400 MHz, DMSO-d₆) δ 13.79-13.40 (m, 1H), 13.10-12.67 (m, 1H),8.75-8.46 (m, 1H), 8.39-8.10 (m, 1H), 8.01-7.71 (m, 1H), 5.24- 4.92 (m,1H), 2.65-2.55 (m, 3H), 2.32-2.22 (m, 1H), 2.35-2.22 (m, 2H), 1.88-1.63(m, 1H), 1.49- 1.19 (m, 2H); LCMS(electrospray) m/z 420.0 (M + H+). D(1S,2S)-N-(5-(5-chloro-6-fluoro-7-methyl-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 212

¹H NMR (400 MHz, DMSO-d₆) δ 13.15-13.72 (m, 1 H) 12.88 (s, 1 H) 8.74 (s,1 H) 8.13-8.21 (m, 2 H) 7.77 (d, J = 7.75 Hz, 1 H) 7.35 (d, J = 7.75 Hz,1 H) 4.92-5.19 (m, 1 H) 3.17 (s, 1 H) 2.65 (s, 3 H) 2.23-2.31 (m, 1H)1.74-1.84 (m, 2 H) 1.31-1.39 (m, 1 H); LCMS(electrospray) m/z 400.0 (M +H+). D (1S,2S)-2-fluoro-N-(5-(7-(methylthio)-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2- yl)cyclopropane-1-carboxamide 213

¹H NMR (400 MHz, DMSO-d₆) δ 13.93 (s, 1H), 8.26 (d, J = 8.4 Hz, 1H),7.96 (s, 1H), 7.74 (d, J = 8.3 Hz, 1H), 5.25-4.89 (m, 1H), 2.31 (d, J =2.8 Hz, 3H), 2.29-2.22 (m, 1H), 1.84-1.70 (m, 1H), 1.29-1.36 (m, J =2.6, 6.2, 12.8 Hz, 1H); LCMS(electrospray) m/z 470.2 (M + H+). D(1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl-7-(trifluoromethoxy)-1H-indazol-4- yl)thiazolo[5,4-b]pyridin-2-yl)cyclopropane-1-carboxamide 214

¹H NMR (400 MHz, DMSO-d₆) δ 13.27 (br s, 1H), 13.01-12.74 (m, 1H), 8.68(br s, 1H), 8.55 (d, J = 8.6 Hz, 1H), 8.22 (d, J = 8.5 Hz, 1H), 8.15 (q,J = 8.6 Hz, 2H), 7.61 (d, J = 14.3 Hz, 1H), 5.18-4.96 (m, 1H), 2.99 (brs, 6H), 2.30-2.23 (m, 1H), 1.83- 1.72 (m, 1H), 1.38-1.31 (m, 1H);LCMS(electrospray) m/z 415.2 (M + H+). D(1S,2S)-N-(5-(7-(dimethylamino)-6- fluoro-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 215

¹H NMR (400 MHz, DMSO-d₆) δ 14.03 (s, 1H), 12.97 (s, 1H), 8.82 (s, 1H),8.26 (s, 2H), 7.90 (d, J = 12.0 Hz, 1H), 5.24-4.94 (m, 1H), 2.28 (ddd, J= 2.0, 4.6, 6.7 Hz, 1H), 1.87-1.70 (m, 1H), 1.32- 1.36 (m, J = 2.6, 6.2,12.7 Hz, 1H); LCMS(electrospray) m/z 456.2 (M + H+). D(1S,2S)-2-fluoro-N-(5-(6-fluoro-7- (trifluoromethoxy)-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2- yl)cyclopropane-1-carboxamide 216

¹H NMR (400 MHz, DMSO-d₆) δ 13.30-12.94 (m, 1H), 8.73-8.65 (m, 1H),8.15-8.08 (m, 1H), 8.07-8.01 (m, 1H), 7.66 (d, J = 7.9 Hz, 1H), 6.82-6.73 (m, 1H), 5.29-4.92 (m, 1H), 3.13-2.82 (m, 6H), 2.29-2.18 (m, 1H),2.07 (s, 1H), 1.84-1.69 (m, 1H), 1.39-1.25 (m, 1H); LCMS(electrospray)m/z 397.1 (M + H+). D (1S,2S)-N-(5-(7-(dimethylamino)-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 217

¹H NMR (400 MHz, DMSO-d₆) δ 13.94-13.07 (m, 1H), 8.24 (d, J = 8.3 Hz,1H), 7.92 (s, 1H), 7.74- 7.44 (m, 2H), 5.18-4.91 (m, 1H), 2.27 (d, J =2.6 Hz, 3H), 2.26-2.22 (m, 1H), 1.82-1.71 (m, 1H), 1.37-1.28 (m, 1H);LCMS(electrospray) m/z 436.1 (M + H+). D(1S,2S)-N-(5-(7-(difluoromethyl)-6- fluoro-5-methyl-1H-indazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 218

¹H NMR (400 MHz, DMSO-d₆) δ 13.33 (br s, 1H), 8.19 (d, J = 8.4 Hz, 1H),7.77 (s, 1H), 7.70 (d, J = 8.4 Hz, 1H), 5.19-4.95 (m, 1H), 3.25 (br d, J= 7.7 Hz, 2H), 2.97 (d, J = 1.6 Hz, 3H), 2.26 (s, 3H), 1.85- 1.70 (m,1H), 1.40-1.21 (m, 2H), 1.10-1.04 (m, 3H); LCMS(electrospray) m/z 475(M + H+). D (1S,2S)-N-(5-(7-(ethyl(methyl)amino)-6-fluoro-5-(methylthio)-1H-indazol-4- yl)thiazolo[5,4-b]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 219

¹H NMR (400 MHz, DMSO-d₆) δ 13.32 (s, 1H), 13.04 (s, 1H), 9.13 (s, 1H),8.31 (s, 1H), 7.79 (s, 1H), 7.52 (d, J = 9.3 Hz, 1H), 5.23-4.94 (m, 1H),2.35-2.17 (m, 4H), 1.86-1.68 (m, 1H), 1.41-1.29 (m, 1H);LCMS(electrospray) m/z 418.0 (M + H+). D(1S,2S)-2-fluoro-N-(6-(6-fluoro-5-(methylthio)-1H-indazol-4-yl)thiazolo[4,5-c]pyridin-2-yl)cyclopropane-1- carboxamide 220

¹H NMR (400 MHz, DMSO-d₆) δ 13.60 (s, 1H), 13.10 (s, 1H), 9.12 (s, 1H),8.53 (s, 1H), 8.14 (s, 1H), 7.63 (d, J = 11.5 Hz, 1H), 5.19-4.96 (m,1H), 3.17 (s, 3H), 2.29-2.21 (m, 1H), 1.86-1.68 (m, 1H), 1.39-1.29 (m,1H); LCMS(electrospray) m/z 434.0 (M + H+). D(1S,2S)-2-fluoro-N-(6-(6-fluoro-5- (methylsulfinyl)-1H-indazol-4-yl)thiazolo[4,5-c]pyridin-2- yl)cyclopropane-1-carboxamide 221

¹H NMR (400 MHz, DMSO-d₆) δ 12.77 (s, 1H), 9.70 (s, 1H), 9.00 (s, 1H),8.66 (d, J = 9.2 Hz, 1H), 8.59 (s, 1H), 8.55 (d, J = 9.2 Hz, 1H), 8.33(d, J = 8.0 Hz, 1H), 8.14 (d, J = 8.8 Hz, 1H), 5.91~5.71 (m, 1H), 3.11(s, 3H), 3.05~3.00 (m, 1H), 2.54~ 2.48 (m, 1H), 2.07~2.03 (m, 1H); LCMS(electrospray) m/z 350.0 (M + H)+. E (1S,2S)-2-fluoro-N-(6-(5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2- yl)cyclopropane-1-carboxamide 222

¹H NMR (400 MHz, DMSO-d₆) δ 13.23 (s, 1H), 11.01 (s, 1H), 8.93 (s, 1H),8.17 (s, 1H), 7.59~7.51 (m, 3H), 7.42 (t, J = 7.8 Hz, 1H), 7.26 (d, J =6.4 Hz, 1H), 5.00~4.79 (m, 1H), 2.13~2.10 (m, 1H), 1.67~1.60 (m, 1H),1.17~1.09 (m, 1H); LCMS (electrospray) m/z 335.9 (M + H)+. E(1S,2S)-N-(6-(1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 223

¹H NMR (400 MHz, METHANOL-d₄) δ 8.92 (s, 1H), 8.13 (s, 1H), 7.99-7.91(m, 3H), 7.68 (dd, J = 1.0, 8.9 Hz, 1H), 7.58 (d, J = 8.9 Hz, 1H), 1.95-1.87 (m, 1H), 1.12-1.07 (m, 2H), 1.05-0.98 (m, 2H); LCMS (electrospray)m/z 352.0 (M + H)+. F N-(6-(5-chloro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2- yl)cyclopropanecarboxamide. 2 HCl salt 224

¹H NMR (400 MHz, METHANOL-d₄) δ 8.98 (s, 1H), 8.17-8.09 (m, 3H), 7.94(d, J = 9.2 Hz, 1H), 7.71 (d, J = 9.2 Hz, 1H), 7.54-7.48 (m, 1H), 3.90(s, 3H), 1.94-1.85 (m, 1H), 1.12-1.06 (m, 2H), 1.05-0.99 (m, 2H); LCMS(electrospray) m/z 348.0 (M + H)+. F N-(6-(5-methoxy-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2- yl)cyclopropanecarboxamide. 2 HCl salt 225

¹H NMR (400 MHz, METHANOL-d₄) δ 8.76 (s, 1H), 7.88-7.83 (m, 2H), 7.75(dd, J = 1.5, 9.2 Hz, 1H), 7.66 (dd, J = 0.8, 8.9 Hz, 1H), 7.36 (d, J =8.9 Hz, 1H), 1.96-1.88 (m, 1H), 1.09-1.04 (m, 2H), 1.02-0.95 (m, 2H);LCMS (electrospray) m/z 333.2 F N-(6-(5-amino-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2- yl)cyclopropanecarboxamide. 3 TFA salt 226

¹H NMR (400 MHz, DMSO-d₆) δ 11.43 (br s, 1H), 8.80 (s, 1H), 8.16 (s,1H), 7.93 (s, 1H), 7.84-7.76 (m, 2H), 7.69 (d, J = 9.4 Hz, 1H), 7.45 (brd, J = 8.9 Hz, 1H), 1.97 (quin, J = 6.2 Hz, 1H), 0.86 (d, J = 6.0 Hz,4H); LCMS (electrospray) m/z 386.1 (M + H)+. FN-(6-(5-(trifluoromethyl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide. 2 HCl salt 227

¹H NMR (400 MHz, DMSO-d₆) δ 11.40 (br s, 1H), 8.83 (s, 1H), 8.14 (s,1H), 7.75 (d, J = 9.0 Hz, 1H), 7.68 (s, 1H), 7.61 (d, J = 9.0 Hz, 1H),7.37 (d, J = 10.9 Hz, 1H), 6.90-5.46 (m, 6H), 1.94 (quin, J = 6.2 Hz,1H), 0.95-0.82 (m, 4H); LCMS (electrospray) m/z 351.2 (M + H)+. FN-(6-(5-amino-6-fluoro-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide. 3TFA salt 228

¹H NMR (400 MHz, METHANOL-d₄) δ 8.56- 8.53 (m, 1H), 8.11 (s, 1H), 7.82(s, 1H), 7.68 (d, J = 8.9 Hz, 1H), 7.58-7.50 (m, 2H), 7.38 (dd, J = 1.7,9.2 Hz, 1H), 1.97-1.88 (m, 1H), 1.02-0.97 (m, 2H), 0.93-0.88 (m, 2H);LCMS (electrospray) m/z 397.9 (M + H)+. F N-(6-(5-bromo-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2- yl)cyclopropanecarboxamide 229

¹H NMR (400 MHz, METHANOL-d₄) δ 8.82 (br s, 1H), 7.89 (br d, J = 8.8 Hz,1H), 7.82-7.73 (m, 3H), 7.45 (d, J = 8.9 Hz, 1H), 2.98 (s, 3H),1.98-1.86 (m, 1H), 1.12-0.95 (m, 4H); LCMS (electrospray) m/z 347.0 (M +H)+. F N-(6-(5-(methylamino)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide. 3 TFA salt 230

¹H NMR (400 MHz, METHANOL-d₄) δ 8.60- 8.57 (m, 1H), 8.09 (s, 1H), 7.87(s, 1H), 7.58-7.49 (m, 3H), 7.48-7.44 (m, 1H), 2.62 (s, 6H), 1.97- 1.89(m, 1H), 1.03-0.97 (m, 2H), 0.94-0.88 (m, 2H); LCMS (electrospray) m/z361.2 (M + H)+. F N-(6-(5-(dimethylamino)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2- yl)cyclopropanecarboxamide 231

¹H NMR (400 MHz, DMSO-d₆) δ 13.49 (br s, 1H), 11.05 (s, 1H), 8.78 (s,1H), 8.14 (s, 1H), 7.92 (s, 1H), 7.64 (d, J = 8.7 Hz, 1H), 7.57 (d, J =9.2 Hz, 1H), 7.32 (dd, J = 1.7, 9.2 Hz, 1H), 2.05-1.86 (m, 1H),0.85-0.79 (m, 4H); LCMS (electrospray) m/z 414.1 (M + H)+. GN-(6-(5-bromo-6-fluoro-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide. 2 TFA salt 232

¹H NMR (400 MHz, METHANOL-d₄) δ 9.17 (s, 1H), 8.22 (s, 1H), 8.21-8.18(m, 1H), 8.06 (d, J = 9.3 Hz, 1H), 7.84 (s, 2H), 1.94-1.87 (m, 1H),1.14-1.09 (m, 2H), 1.07-1.01 (m, 2H); LCMS (electrospray) m/z 343.0 (M +H)+. F N-(6-(5-cyano-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide. 2 HCl salt 233

¹H NMR (400 MHz, METHANOL-d₄) δ 8.91 (s, 1H), 8.10 (s, 1H), 8.07-8.03(m, 1H), 8.00-7.96 (m, 1H), 7.91 (s, 1H), 7.72-7.65 (m, 2H), 4.61 (s,2H), 3.61 (s, 1H), 1.93-1.86 (m, 1H), 1.13-1.08 (m, 2H), 1.07-1.01 (m,2H); LCMS (electrospray) m/z 348.2 (M + H)+. FN-(6-(5-(hydroxymethyl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide. 2 HCl salt 234

¹H NMR (400 MHz, METHANOL-d₄) δ 8.82 (s, 1H), 8.10 (s, 1H), 8.01-7.95(m, 1H), 7.95-7.89 (m, 1H), 7.78 (s, 1H), 7.64 (d, J = 8.7 Hz, 1H), 7.50(d, J = 8.7 Hz, 1H), 2.69 (q, J = 7.5 Hz, 2H), 1.93- 1.85 (m, 1H), 1.19(t, J = 7.5 Hz, 3H), 1.13-1.07 (m, 2H), 1.07-0.98 (m, 2H); LCMS(electrospray) m/z 346.2 (M + H)+. F N-(6-(5-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2- yl)cyclopropanecarboxamide. 2 HCl salt 235

¹H NMR (400 MHz, DMSO-d₆) δ 11.82 (br s, 1H), 8.90 (s, 1H), 8.19 (s,1H), 7.91 (d, J = 0.6 Hz, 1H), 7.83 (d, J = 9.2 Hz, 1H), 7.63 (br d, J =9.2 Hz, 1H), 7.50 (d, J = 11.4 Hz, 1H), 6.54 (dd, J = 11.9, 17.9 Hz,1H), 5.63 (br d, J = 17.9 Hz, 1H), 5.42 (br d, J = 11.6 Hz, 1H),2.06-1.94 (m, 1H), 0.95-0.85 (m, 4H); LCMS (electrospray) m/z 362.1 (M +H)+. F N-(6-(6-fluoro-5-vinyl-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide. 2 HCl salt 236

¹H NMR (400 MHz, DMSO-d₆) δ 11.46 (br s, 1H), 8.82 (s, 1H), 8.20 (s,1H), 7.94 (s, 1H), 7.85-7.76 (m, 2H), 7.71 (br d, J = 9.2 Hz, 1H), 7.47(br d, J = 8.6 Hz, 1H), 5.11-4.85 (m, 1H), 2.20 (td, J = 6.9, 13.9 Hz,1H), 1.77-1.63 (m, 1H), 1.31-1.16 (m, 1H), 1.31-1.16 (m, 1H); LCMS(electrospray) m/z 403.8 (M + H)+. F (1S,2S)-2-fluoro-N-(6-(5-(trifluoromethyl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide. 2 HCl salt 237

¹H NMR (400 MHz, DMSO-d₆) δ 13.40 (s, 1H), 11.05 (s, 1H), 8.77 (s, 1H),8.16 (s, 1H), 7.91 (s, 1H), 7.62 (d, J = 9.7 Hz, 1H), 7.58-7.48 (m, 2H),7.34 (dd, J = 1.7, 9.2 Hz, 1H), 5.04-4.80 (m, 1H), 2.20-2.10 (m, 1H),1.73-1.59(m, 1H), 1.23-1.10 (m, 1H); LCMS (electrospray) m/z 370.1 (M +H)+. F (1S,2S)-N-(6-(5-chloro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 238

¹H NMR (400 MHz, DMSO-d₆) δ 11.49 (br s, 1H), 8.88 (br s, 1H), 8.20 (s,1H), 7.90 (s, 1H), 7.73 (br d, J = 9.2 Hz, 1H), 7.69-7.64 (m, 1H),7.63-7.53 (m, 2H), 5.11-4.86 (m, 1H), 2.19 (br s, 1H), 1.77- 1.62 (m,1H), 1.22 (br d, J = 2.9 Hz, 1H); LCMS (electrospray) m/z 415.8 (M +H)+. F (1S,2S)-N-(6-(5-bromo-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 2HCl salt 239

¹H NMR (400 MHz, DMSO-d₆) δ 11.69 (br s, 1H), 8.84 (s, 1H), 8.17 (s,1H), 8.04 (s, 1H), 7.88 (d, J = 8.8 Hz, 1H), 7.77 (br d, J = 9.0 Hz,1H), 7.71 (d, J = 8.8 Hz, 1H), 7.59 (br d, J = 8.8 Hz, 1H), 2.40 (s,3H), 2.03-1.95 (m, 1H), 0.95-0.87 (m, 4H); LCMS (electrospray) m/z 359.9(M + H)+. F N-(6-(5-acetyl-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide. 2 HCl salt 240

¹H NMR (400 MHz, DMSO-d₆) δ 12.27 (s, 1H), 8.99 (s, 1H), 8.21 (s, 1H),7.98 (d, J = 9.2 Hz, 1H), 7.85 (dd, J = 1.5, 9.1 Hz, 1H), 7.69 (dd, J =1.0, 8.1 Hz, 2H), 6.23-5.16 (m, 6H), 2.13-2.00 (m, 1H), 1.04-0.87 (m,4H); LCMS (electrospray) m/z 367.0 (M + H+) FN-(6-(5-amino-6-chloro-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide. 3 HCl salt 241

¹H NMR (400 MHz, DMSO-d₆) δ 12.09 (br s, 1H), 9.04 (s, 1H), 8.22 (s,1H), 7.97-7.86 (m, 3H), 7.41 (d, J = 10.5 Hz, 1H), 2.07-2.00 (m, 1H),1.99-1.91 (m, 1H), 1.99-1.91 (m, 1H), 0.97-0.87 (m, 4H), 0.78-0.68 (m,2H), 0.26 (br d, J = 4.5 Hz, 2H); LCMS (electrospray) m/z 376.1 (M + H+)F N-(6-(5-cyclopropyl-6-fluoro-1H-indazol- 4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide. 2 HCl salt 242

¹H NMR (400 MHz, DMSO-d₆) δ 13.50 (br s, 1H), 11.17 (s, 1H), 8.68 (d, J= 7.2 Hz, 1H), 7.92 (s, 1H), 7.79 (d, J = 1.0 Hz, 1H), 7.68 (dd, J =0.9, 9.0 Hz, 1H), 6.97 (s, 1H), 6.96 (d, J = 2.0 Hz, 1H), 6.96- 6.93 (m,1H), 2.13-2.00 (m, 1H), 1.04-0.87 (m, 4H); LCMS (electrospray)m/z 370.8(M + H+) F N-(6-(5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2- yl)cyclopropanecarboxamide. 2 HCl salt 243

¹H NMR (400 MHz, DMSO-d₆) δ 11.91-11.45 (m, 1H), 9.05-8.93 (m, 1H), 8.24(br s, 1H), 8.00 (s, 1H), 7.87-7.59 (m, 3H), 5.07 (br s, 1H), 4.91 (brs, 1H), 2.22 (br s, 1H), 1.79-1.63 (m, 1H), 1.23 (br s, 1H); LCMS(electrospray) m/z 388.0 (M + H+) F (1S,2S)-N-(6-(5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 HCl salt 244

¹H NMR (400 MHz, DMSO-d₆) δ 11.99 (br s, 1H), 8.99 (s, 1H), 8.23 (s,1H), 7.95-7.85 (m, 2H), 7.82 (d, J = 0.9 Hz, 1H), 7.55 (d, J = 8.7 Hz,1H), 7.08 (d, J = 8.7 Hz, 1H), 2.07-1.89 (m, 2H), 0.98-0.90 (m, 4H),0.87-0.81 (m, 2H), 0.69-0.63 (m, 2H); LCMS (electrospray) m/z 358.0 (M +H+) F N-(6-(5-cyclopropyl-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide. 2 HCl salt 245

¹H NMR (400 MHz, DMSO-d₆) δ 11.27 (br s, 1H), 8.78 (s, 1H), 8.14 (s,1H), 7.82 (s, 1H), 7.67 (br d, J = 9.0 Hz, 1H), 7.46 (br d, J = 9.0 Hz,1H), 7.40 (br d, J = 9.8 Hz, 1H), 2.21 (br d, J = 1.2 Hz, 3H), 2.00-1.88 (m, 1H), 0.86 (br d, J = 5.7 Hz, 4H); LCMS (electrospray) m/z 350.2(M + H+) F N-(6-(6-fluoro-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2- yl)cyclopropanecarboxamide. 2 TFA salt 246

¹H NMR (400 MHz, DMSO-d₆) δ 11.30 (s, 1H), 8.73 (s, 1H), 8.15 (s, 1H),7.71-7.65 (m, 2H), 7.40 (br d, J = 11.8 Hz, 2H), 3.04 (td, J = 7.0, 14.1Hz, 1H), 1.98-1.92 (m, 1H), 1.28 (dd, J = 6.9, 17.4 Hz, 6H), 0.87 (d, J= 6.1 Hz, 4H); LCMS (electrospray) m/z 378.1 (M + H+) FN-(6-(6-fluoro-5-isopropyl-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide. 2 TFA salt 247

¹H NMR (400 MHz, DMSO-d₆) δ 12.22 (s, 1H), 8.99 (s, 1H), 8.24 (s, 1H),7.98-7.91 (m, 1H), 7.90- 7.84 (m, 2H), 7.71-7.65 (m, 1H), 7.62-7.57 (m,1H), 2.40 (s, 3H), 2.11-1.99 (m, 1H), 1.05-0.87 (m, 4H); LCMS(electrospray) m/z 364.1 (M + H+) F N-(6-(5-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2- yl)cyclopropanecarboxamide. 2 HCl salt 248

¹H NMR (400 MHz, DMSO-d₆) δ 12.18 (s, 1H), 8.95 (s, 1H), 8.24 (s, 1H),7.95 (d, J = 9.0 Hz, 1H), 7.81-7.74 (m, 2H), 7.46 (d, J = 10.3 Hz, 1H),2.58 (q, J = 6.8 Hz, 2H), 2.09-2.00 (m, 1H), 1.09 (t, J = 7.3 Hz, 3H),0.98-0.87 (m, 4H); LCMS (electrospray) m/z 364.1 (M + H+) FN-(6-(5-ethyl-6-fluoro-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide. 2 HCl salt 249

¹H NMR (400 MHz, DMSO-d₆) δ 13.53 (br s, 1H), 11.13 (s, 1H), 8.72 (s,1H), 8.15 (s, 1H), 7.97 (s, 1H), 7.78-7.74 (m, 1H), 7.73-7.69 (m, 1H),7.63 (d, J = 9.2 Hz, 1H), 7.34 (d, J = 9.0 Hz, 1H), 7.11- 6.80 (m, 1H),2.00-1.91 (m, 1H), 0.87-0.81 (m, 4H); LCMS (electrospray) m/z 368.2 (M +H+) F N-(6-(5-(difluoromethyl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide. 2 TFA salt 250

¹H NMR (400 MHz, DMSO-d₆) δ 13.16 (s, 1H), 11.06 (s, 1H), 8.70 (s, 1H),8.15 (s, 1H), 7.80 (s, 1H), 7.56 (d, J = 9.2 Hz, 1H), 7.38 (d, J = 9.8Hz, 1H), 7.29 (dd, J = 1.7, 9.2 Hz, 1H), 5.09-4.77 (m, 1H), 2.22 (d, J =2.4 Hz, 3H), 2.18-2.11 (m, 1H), 1.75-1.58 (m, 1H), 1.24-1.06 (m, 1H);LCMS (electrospray) m/z 368.1 (M + H+) F(1S,2S)-2-fluoro-N-(6-(6-fluoro-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2- yl)cyclopropane-1-carboxamide251

¹H NMR (400 MHz, DMSO-d₆) δ 11.92 (br s, 1H), 8.99 (s, 1H), 8.21 (s,1H), 7.96-7.81 (m, 3H), 7.46 (d, J = 9.9 Hz, 1H), 4.43 (s, 2H),2.07-1.96 (m, 1H), 0.96-0.87 (m, 4H); LCMS (electrospray) m/z 366.1 (M +H+) F N-(6-(6-fluoro-5-(hydroxymethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2- yl)cyclopropanecarboxamide. 2 HClsalt 252

¹H NMR (400 MHz, METHANOL-d₄) δ 9.03 (s, 1H), 8.18-8.14 (m, 1H), 8.05(s, 1H), 7.99 (d, J = 9.2 Hz, 1H), 7.49 (d, J = 10.6 Hz, 1H), 3.77 (s,3H), 1.95-1.82 (m, 1H), 1.15-1.07 (m, 2H), 1.06- 1.00 (m, 2H); LCMS(electrospray) m/z 366.1 (M + H+) FN-(6-(6-fluoro-5-methoxy-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide. 2 HCl salt 253

¹H NMR (400 MHz, DMSO-d₆) δ 13.64 (s, 1H), 11.16 (s, 1H), 8.76 (s, 1H),8.19 (s, 1H), 7.98 (s, 1H), 7.66-7.57 (m, 2H), 7.29 (dd, J = 1.8, 9.1Hz, 1H), 7.13-6.78 (m, 1H), 5.07-4.80 (m, 1H), 2.16 (td, J = 6.9, 13.9Hz, 1H), 1.74-1.61 (m, 1H), 1.24- 1.13 (m, 1H); LCMS (electrospray) m/z404.0 (M + H+) F (1S,2S)-N-(6-(5-(difluoromethyl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA salt 254

¹H NMR (400 MHz, DMSO-d₆) δ 13.50 (s, 1H), 11.11 (s, 1H), 8.79 (s, 1H),8.17 (s, 1H), 7.93 (s, 1H), 7.65 (d, J = 8.8 Hz, 1H), 7.57 (d, J = 9.2Hz, 1H), 7.32 (dd, J = 1.6, 7.6 Hz, 1H), 5.02 (m, 0.5H), 4.85 (m, 0.5H),2.16 (m, 1H), 1.66 (m, 1H), 1.16 (m, 1H), LCMS (electrospray) m/z 433.00(M + H)+. F (1S,2S)-N-(6-(5-bromo-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 255

¹H NMR (400 MHz, DMSO-d₆) δ 13.59 (br s, 1H), 11.04 (s, 1H), 8.72 (s,1H), 8.15 (s, 1H), 7.97 (s, 1H), 7.62-7.56 (m, 2H), 7.23 (dd, J = 1.7,9.1 Hz, 1H), 7.11-6.80 (m, 1H), 2.01-1.92 (m, 1H), 0.85- 0.79 (m, 4H);LCMS (electrospray) m/z 386.1 (M + H+) F N-(6-(5-(difluoromethyl)-6-fluoro-1H-indazol- 4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide 256

¹H NMR (400 MHz, DMSO-d₆) δ 14.14 (s, 1H), 11.13 (s, 1H), 8.87-8.83 (m,1H), 8.19 (s, 1H), 8.15 (br s, 1H), 7.61 (d, J = 9.3 Hz, 1H), 7.40 (dd,J = 1.8, 9.2 Hz, 1H), 5.04-4.83 (m, 1H), 2.19- 2.13 (m, 1H), 1.72-1.62(m, 1H), 1.23-1.15 (m, 1H); LCMS (electrospray) m/z 422.1 (M + H)+. F(1S,2S)-N-(6-(5,7-dichloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA salt 257

¹H NMR (400 MHz, DMSO-d₆) δ 13.36 (s, 1H), 11.19 (br s, 1H), 8.72 (s,1H), 8.16 (s, 1H), 7.80 (s, 1H), 7.62 (d, J = 9.2 Hz, 1H), 7.37 (br d, J= 9.2 Hz, 1H), 5.10-4.79 (m, 1H), 2.48 (d, J = 1.7 Hz, 3H), 2.21 (d, J =2.8 Hz, 3H), 2.18-2.10 (m, 1H), 1.75- 1.61 (m, 1H), 1.27-1.10 (m, 1H);LCMS (electrospray) m/z 382.4 (M + H)+. F(1S,2S)-2-fluoro-N-(6-(6-fluoro-5,7-dimethyl-1H-indazol-4-yl)imidazo[1,2- a]pyridin-2-yl)cyclopropane-1-carboxamide. 2 TFA salt 258

¹H NMR (400 MHz, DMSO-d₆)) δ 13.55 (br s, 1H), 11.21 (s, 1H), 8.80 (s,1H), 8.17 (s, 1H), 7.95 (s, 1H), 7.62 (d, J = 9.2 Hz, 1H), 7.43 (d, J =9.2 Hz, 1H), 5.08-4.77 (m, 1H), 3.01 (s, 3H), 3.00 (s, 3H), 2.16 (td, J= 7.0, 13.8 Hz, 1H), 1.76-1.57 (m, 1H), 1.27-1.11 (m, 1H); LCMS(electrospray) m/z 431.2 (M + H)+. H (1S,2S)-N-(6-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA salt 259

¹H NMR (400 MHz, DMSO-d₆) δ 11.20 (br s, 1H), 8.88 (s, 1H), 8.21 (s,1H), 8.09 (d, J = 1.1 Hz, 1H), 7.66 (br d, J = 8.3 Hz, 1H), 7.46 (br d,J = 8.8 Hz, 1H), 5.11-4.81 (m, 1H), 2.23-2.11 (m, 1H), 1.96 (s, 3H),1.93 (s, 3H), 1.75-1.62 (m, 1H), 1.25- 1.13 (m, 1H); LCMS (electrospray)m/z 464.1 (M + H)+. H (1S,2S)-N-(6-(5-chloro-7-(dimethylphosphoryl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA salt 260

¹H NMR (400 MHz, DMSO-d₆) δ 14.17-13.29 (m, 1H), 11.18 (s, 1H), 8.75 (s,1H), 8.16 (s, 1H), 7.97 (s, 1H), 7.61 (d, J = 9.0 Hz, 1H), 7.36 (dd, J =1.3, 9.2 Hz, 1H), 5.12-4.77 (m, 1H), 2.26 (d, J = 2.9 Hz, 3H), 2.16 (td,J = 7.0, 14.0 Hz, 1H), 1.76- 1.58 (m, 1H), 1.25-1.10 (m, 1H); LCMS(electrospray) m/z 402.0 (M + H)+. H(1S,2S)-N-(6-(7-chloro-6-fluoro-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA salt 261

¹H NMR (400 MHz, DMSO-d₆) δ 11.29 (s, 1H), 8.89 (s, 1H), 8.20 (s, 1H),8.17 (s, 1H), 7.67 (d, J = 9.0 Hz, 1H), 7.50 (br d, J = 9.4 Hz, 1H),5.09- 4.82 (m, 1H), 2.18 (td, J = 6.9, 13.9 Hz, 1H), 1.75- 1.62 (m, 1H),1.26-1.14 (m, 1H); LCMS (electrospray) m/z 466.1 (M + H)+. H(1S,2S)-N-(6-(7-bromo-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 HCl salt 262

¹H NMR (400 MHz, DMSO-d₆) δ 11.19 (s, 1H), 8.73 (s, 1H), 8.15 (s, 1H),7.95 (br s, 1H), 7.61 (d, J = 9.3 Hz, 1H), 7.35 (d, J = 7.8 Hz, 1H),5.17-4.75 (m, 1H), 2.25 (d, J = 2.9 Hz, 3H), 2.28-2.12 (m, 1H),1.72-1.59 (m, 1H), 1.24-1.10 (m, 1H); LCMS (electrospray) m/z 386.3 (M +H)+. H (1S,2S)-N-(6-(6,7-difluoro-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA salt 263

¹H NMR (400 MHz, METHANOL-d₄) δ 8.78 (s, 1H), 7.93 (s, 1H), 7.85 (d, J =9.2 Hz, 1H), 7.71 (d, J = 9.5 Hz, 1H), 5.06-4.94 (m, 1H), 2.31 (d, J =3.1 Hz, 3H), 2.16-2.09 (m, 1H), 1.93-1.79 (m, 1H), 1.33-1.22 (m, 1H);LCMS (electrospray) m/z 436.0 (M + H)+. H(1S,2S)-2-fluoro-N-(6-(6-fluoro-5-methyl-7-(trifluoromethyl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide. 2 TFA salt 264

¹H NMR (400 MHz, DMSO-d₆) δ 13.38 (br s, 1H), 11.28 (br s, 1H), 8.75 (s,1H), 8.16 (s, 1H), 7.85 (s, 1H), 7.64 (d, J = 9.0 Hz, 1H), 7.52 (s, 1H),7.44 (br d, J = 9.0 Hz, 1H), 7.14 (dd, J = 11.4, 17.7 Hz, 1H), 6.12 (brd, J = 17.9 Hz, 1H), 5.51 (d, J = 11.5 Hz, 1H), 5.07-4.86 (m, 1H), 2.34(s, 3H), 2.16 (td, J = 7.0, 13.8 Hz, 1H), 1.76-1.60 (m, 1H), 1.20 (tdd,J = 6.4, 9.1, 12.3 Hz, 1H); LCMS (electrospray) m/z 376.1 (M + H)+. H(1S,2S)-2-fluoro-N-(6-(5-methyl-7-vinyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2- yl)cyclopropane-1-carboxamide.2TFA salt 265

¹H NMR (400 MHz, DMSO-d₆) δ 13.09 (br s, 1H), 11.12 (s, 1H), 8.72 (s,1H), 8.15 (s, 1H), 7.90 (br s, 1H), 7.56 (d, J = 9.2 Hz, 1H), 7.35 (brd, J = 9.2 Hz, 1H), 5.11-4.75 (m, 1H), 3.17 (br d, J = 2.1 Hz, 3H), 2.16(td, J = 6.9, 13.8 Hz, 1H), 1.74-1.60 (m, 1H), 1.25-1.11 (m, 1H); LCMS(electrospray) m/z 417.1 (M + H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-(methylamino)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA salt 266

¹H NMR (400 MHz, DMSO-d₆) δ 13.79 (br s, 1H), 11.14 (s, 1H), 8.84 (s,1H), 8.19 (s, 1H), 8.06 (s, 1H), 7.61 (d, J = 9.3 Hz, 1H), 7.41 (dd, J =1.6, 9.3 Hz, 1H), 5.08-4.80 (m, 1H), 2.58 (s, 3H), 2.22- 2.11 (m, 1H),1.74-1.60 (m, 1H), 1.18 (tdd, J = 6.2, 9.1, 12.4 Hz, 1H); LCMS(electrospray) m/z 434.2 (M + H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA salt 267

¹H NMR (400 MHz, DMSO-d₆) δ 13.52 (br s, 1H), 11.19 (s, 1H), 8.90 (s,1H), 8.22 (d, J = 3.4 Hz, 2H), 7.65 (d, J = 9.3 Hz, 1H), 7.44 (dd, J =1.7, 9.3 Hz, 1H), 5.07-4.80 (m, 1H), 3.56 (s, 3H), 2.21-2.14 (m, 1H),1.72-1.62 (m, 1H), 1.24-1.15 (m, 1H); LCMS (electrospray) m/z 466.1 (M +H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7- (methylsulfonyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 2TFA salt 268

¹H NMR (400 MHz, DMSO-d₆) δ 11.29 (s, 1H), 8.78 (s, 1H), 8.17 (s, 1H),7.99 (s, 1H), 7.65 (d, J = 9.1 Hz, 1H), 7.42 (dd, J = 1.6, 9.1 Hz, 1H),5.08-4.84 (m, 1H), 2.26 (d, J = 3.0 Hz, 3H), 2.21- 2.11 (m, 1H),1.75-1.62 (m, 1H), 1.20 (tdd, J = 6.3, 9.0, 12.4 Hz, 1H); LCMS(electrospray) m/z 446.2 (M + H)+. H(1S,2S)-N-(6-(7-bromo-6-fluoro-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA salt 269

¹H NMR (400 MHz, DMSO-d₆) δ 11.22 (s, 1H), 8.76 (s, 1H), 8.16 (s, 1H),7.89 (s, 1H), 7.64 (d, J = 9.0 Hz, 1H), 7.41 (dd, J = 1.6, 9.1 Hz, 1H),5.06- 5.02 (m, 1H), 4.90-4.84 (m, 1H), 2.52 (s, 3H), 2.23 (d, J = 2.9Hz, 3H), 2.20-2.12 (m, 1H), 1.75- 1.63 (m, 1H), 1.26-1.14 (m, 1H); LCMS(electrospray) m/z 414.1 (M + H)+. H(1S,2S)-2-fluoro-N-(6-(6-fluoro-5-methyl- 7-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2- yl)cyclopropane-1-carboxamide. 2 TFA salt270

¹H NMR (400 MHz, DMSO-d₆) δ 13.23 (br s, 1H), 11.20 (s, 1H), 8.79 (s,1H), 8.19 (s, 1H), 8.03 (s, 1H), 7.64 (d, J = 9.2 Hz, 1H), 7.37 (dd, J =1.7, 9.1 Hz, 1H), 5.06-4.84 (m, 1H), 3.50 (br s, 3H), 2.27 (d, J = 2.8Hz, 3H), 2.21-2.12 (m, 1H), 1.73-1.62 (m, 1H), 1.23-1.14 (m, 1H); LCMS(electrospray) m/z 446.2 (M + H)+. H(1S,2S)-2-fluoro-N-(6-(6-fluoro-5-methyl-7-(methylsulfonyl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide. 2 TFA salt 271

¹H NMR (400 MHz, DMSO-d₆) δ 13.54 (br s, 1H), 11.27 (s, 1H), 8.73 (s,1H), 8.16 (s, 1H), 7.84 (s, 1H), 7.64 (d, J = 9.3 Hz, 1H), 7.41 (dd, J =1.4, 9.1 Hz, 1H), 5.13-4.79 (m, 1H), 4.08 (d, J = 1.0 Hz, 3H), 2.22 (d,J = 3.1 Hz, 3H), 2.20-2.10 (m, 1H), 1.77-1.60 (m, 1H), 1.20 (tdd, J =6.3, 9.1, 12.4 Hz, 1H); LCMS (electrospray) m/z 398.2 (M + H)+. H(1S,2S)-2-fluoro-N-(6-(6-fluoro-7- methoxy-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2- yl)cyclopropane-1-carboxamide. 2 TFA salt272

¹H NMR (400 MHz, DMSO-d₆) δ 13.81 (br s, 1H), 11.15 (s, 1H), 8.80 (s,1H), 8.17 (s, 1H), 8.00 (s, 1H), 7.61 (d, J = 9.3 Hz, 1H), 7.39 (dd, J =1.6, 9.2 Hz, 1H), 5.12-4.81 (m, 1H), 4.16 (d, J = 1.5 Hz, 3H), 2.22-2.11(m, 1H), 1.75-1.60 (m, 1H), 1.18 (tdd, J = 6.3, 9.1, 12.4 Hz, 1H); LCMS(electrospray) m/z 418.2 (M + H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-methoxy-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA salt 273

¹H NMR (400 MHz, DMSO-d₆) δ 10.90 (br s, 1H), 8.63 (s, 1H), 8.13 (s,1H), 7.73 (s, 1H), 7.61 (d, J = 9.0 Hz, 1H), 7.36 (d, J = 9.2 Hz, 1H),5.03-4.80 (m, 1H), 3.00 (s, 6H), 2.19 (d, J = 2.9 Hz, 3H), 2.18- 2.14(m, 1H), 1.78-1.65 (m, 1H), 1.24-1.14 (m, 1H); LCMS (electrospray) m/z411.2 (M + H)+. H (1S,2S)-N-(6-(7-(dimethylamino)-6-fluoro-5-methyl-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA salt 274

¹H NMR (400 MHz, DMSO-d₆) δ 11.29 (s, 1H), 10.19 (s, 1H), 8.75 (s, 1H),8.16 (s, 1H), 7.82 (s, 1H), 7.66 (s, 1H), 7.64 (s, 1H), 7.45 (br d, J =9.9 Hz, 1H), 6.61-6.51 (m, 1H), 6.35 (dd, J = 1.8, 16.9 Hz, 1H),5.89-5.84 (m, 1H), 5.08-5.03 (m, 1H), 4.89 (dt, J = 3.8, 6.3 Hz, 1H),2.32 (s, 3H), 2.21- 2.12 (m, 1H), 1.76-1.60 (m, 1H), 1.27-1.14 (m, 1H);LCMS (electrospray) m/z 419.3 (M + H)+. H(1S,2S)-N-(6-(7-acrylamido-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA salt 275

¹H NMR (400 MHz, DMSO-d₆) δ 13.80 (br s, 1H), 11.18 (s, 1H), 8.82 (s,1H), 8.17 (s, 1H), 8.00 (s, 1H), 7.62 (d, J = 9.2 Hz, 1H), 7.42 (dd, J =1.5, 9.3 Hz, 1H), 5.11-4.81 (m, 1H), 4.40 (q, J = 7.1 Hz, 2H), 2.21-2.10(m, 1H), 1.74-1.61 (m, 1H), 1.41 (t, J = 7.0 Hz, 3H), 1.25-1.09 (m, 1H);LCMS (electrospray) m/z 432.3 (M + H)+. H(1S,2S)-N-(6-(5-chloro-7-ethoxy-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA salt 276

¹H NMR (400 MHz, DMSO-d₆) δ 11.23-11.08 (m, 1H), 10.40-10.29 (m, 1H),8.80 (s, 1H), 8.17 (s, 1H), 8.01 (br d, J = 7.9 Hz, 2H), 7.59 (br d, J =9.0 Hz, 1H), 7.46-7.36 (m, 1H), 6.66-6.49 (m, 1H), 6.41-6.36 (m, 1H),5.95-5.85 (m, 1H), 5.12-4.78 (m, 1H), 2.22-2.08 (m, 1H), 1.77-1.58 (m,1H), 1.27-1.10 (m, 1H); LCMS (electrospray) m/z 439.2 (M + H)+. H(1S,2S)-N-(6-(7-acrylamido-5-chloro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA salt 277

¹H NMR (400 MHz, DMSO-d₆) δ 11.14 (s, 1H), 9.88 (br d, J = 6.7 Hz, 1H),8.77 (dd, J = 1.0, 1.6 Hz, 1H), 8.19 (s, 1H), 8.03 (br s, 1H), 7.60 (d,J = 9.2 Hz, 1H), 7.36 (dd, J = 1.8, 9.2 Hz, 1H), 5.05- 5.00 (m, 1H),4.86 (dt, J = 3.9, 6.2 Hz, 1H), 3.58 (br d, J = 11.0 Hz, 4H), 3.53-3.44(m, 2H), 3.39- 3.26 (m, 2H), 2.93 (br d, J = 2.7 Hz, 3H), 2.20- 2.12 (m,1H), 1.73-1.61 (m, 1H), 1.24-1.13 (m, 1H); LCMS (electrospray) m/z 486.2(M + H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-(4-methylpiperazin-1-yl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 3 TFA 278

¹H NMR (400 MHz, DMSO-d₆) δ 13.09 (br s, 1H), 10.92 (s, 1H), 8.64 (s,1H), 8.13 (s, 1H), 7.75 (s, 1H), 7.52 (d, J = 9.2 Hz, 1H), 7.48 (d, J =8.3 Hz, 1H), 7.32 (d, J = 8.6 Hz, 1H), 7.26 (dd, J = 1.7, 9.2 Hz, 1H),4.46 (t, J = 5.2 Hz, 1H), 3.69-3.60 (m, 1H), 3.55-3.48 (m, 1H), 2.32 (s,3H), 2.08-1.99 (m, 1H), 1.49-1.39 (m, 1H), 1.02-0.96 (m, 1H), 0.95-0.90(m, 1H); LCMS (electrospray) m/z 362.3 (M + H)+. H2-(hydroxymethyl)-N-(6-(5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2- yl)cyclopropane-1-carboxamide 279

¹H NMR (400 MHz, DMSO-d₆) δ 13.54 (br s, 1H), 11.21 (s, 1H), 8.81 (s,1H), 8.18 (s, 1H), 7.98 (s, 1H), 7.62 (d, J = 9.3 Hz, 1H), 7.43 (dd, J =1.6, 9.2 Hz, 1H), 5.07-4.84 (m, 1H), 3.84-3.82 (m, 4H), 3.29 (br s, 4H),2.21-2.12 (m, 1H), 1.74-1.61(m, 1H), 1.19 (tdd, J = 6.4, 9.1, 12.4 Hz,1H); LCMS (electrospray) m/z 473.2 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-morpholino-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA 280

¹H NMR (400 MHz, DMSO-d₆) δ 11.23 (1 H, s) 8.78 (1 H, s) 8.16 (1 H, s)7.93 (1 H, br s) 7.61 (1 H, d, J = 9.20 Hz) 7.44 (1 H, br d, J = 9.40Hz) 5.16- 4.71 (1 H, m) 2.17 (1 H, dt, J = 14.07, 6.97 Hz) 1.76-1.61 (1H, m) 1.27-1.17 (4 H, m); LCMS (electrospray) m/z 431.0 (M + H)+. H(1S,2S)-N-(6-(5-chloro-7-(ethylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA 281

¹H NMR (400 MHz, DMSO-d₆) δ 13.50 (1 H, br s) 11.38-11.10 (1 H, m)8.99-8.77 (1 H, m) 8.17 (1 H, s) 7.96 (1 H, s) 7.77-7.57 (1 H, m)7.53-7.35 (1 H, m) 5.14-4.79 (1 H, m) 3.39-3.37 (1 H, m) 3.30 (4 H, q, J= 7.01 Hz) 2.17 (1 H, dt, J = 13.88, 7.00 Hz) 1.79-1.59 (1 H, m)1.27-1.12 (1 H, m) 1.06-0.95 (6 H, m); LCMS (electrospray) m/z 459.0(M + H)+. H (1S,2S)-N-(6-(5-chloro-7-(diethylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA 282

¹H NMR (400 MHz, DMSO-d₆) δ 13.15 (br s, 1H), 11.16 (s, 1H), 8.74 (s,1H), 8.16 (s, 1H), 7.93 (br s, 1H), 7.58 (d, J = 9.0 Hz, 1H), 7.37 (dd,J = 1.5, 9.2 Hz, 1H), 5.07-4.82 (m, 1H), 3.72 (br s, 4H), 2.21- 2.12 (m,1H), 1.98-1.93 (m, 4H), 1.73-1.62 (m, 1H), 1.24-1.13 (m, 1H); LCMS(electrospray) m/z 457.3 (M + H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-(pyrrolidin-1-yl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 283

¹H NMR (400 MHz, DMSO-d₆) δ13.08 (br s, 1H), 11.08 (s, 1H), 8.70 (s,1H), 8.14 (s, 1H), 7.89 (br s, 1H), 7.54 (d, J = 9.3 Hz, 1H), 7.30 (dd,J = 1.6, 9.3 Hz, 1H), 5.06-4.79 (m, 1H), 4.39 (br t, J = 5.7 Hz, 4H),2.39-2.32 (m, 2H), 2.15 (td, J = 7.0, 13.7 Hz, 1H), 1.72-1.61 (m, 1H),1.22-1.13 (m, 1H); LCMS (electrospray) m/z 443.4 (M + H)+. H(1S,2S)-N-(6-(7-(azetidin-1-yl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 284

¹H NMR (400 MHz, DMSO-d₆) δ 11.22-11.10 (m, 1H), 8.76 (br s, 1H), 8.17(s, 1H), 7.62-7.56 (m, 2H), 7.43-7.32 (m, 1H), 6.87 (s, 1H), 5.07- 4.83(m, 1H), 2.21-2.10 (m, 1H), 1.75-1.60 (m, 1H), 1.25-1.13 (m, 1H);LCMS(electrospray) m/z 385.4 (M + H+). H(1S,2S)-N-(6-(6-amino-5-chloro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 285

¹H NMR (400 MHz, DMSO-d₆) δ 13.36 (br s, 1H), 11.28 (s, 1H), 8.69 (s,1H), 8.15 (s, 1H), 7.73 (s, 1H), 7.63 (d, J = 9.1 Hz, 1H), 7.43 (br d, J= 9.1 Hz, 1H), 6.83 (s, 1H), 5.08-4.86 (m, 1H), 3.99 (s, 3H), 2.32 (s,3H), 2.21-2.12 (m, 1H), 1.75-1.63 (m, 1H), 1.27-1.12 (m, 1H);LCMS(electrospray) m/z 380.5 (M + H+). H(1S,2S)-2-fluoro-N-(6-(7-methoxy-5- methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1- carboxamide. 2 TFA 286

¹H NMR (400 MHz, DMSO-d₆) δ 13.53-13.11 (m, 1H), 11.23-11.11 (m, 1H),9.82 (s, 1H), 8.80 (br s, 1H), 8.17 (d, J = 11.5 Hz, 2H), 7.89 (s, 1H),7.65-7.57 (m, 1H), 7.43-7.32 (m, 1H), 6.72 (dd, J = 10.3, 17.1 Hz, 1H),6.32 (dd, J = 1.9, 17.0 Hz, 1H), 5.85-5.80 (m, 1H), 5.07-4.83 (m, 1H),2.20- 2.12 (m, 1H), 1.73-1.61 (m, 1H), 1.23-1.14 (m, 1H); LCMS(electrospray) m/z 439.3 (M + H+). H(1S,2S)-N-(6-(6-acrylamido-5-chloro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 287

¹H NMR (400 MHz, DMSO-d₆) δ 13.30 (br s, 1H), 11.29 (s, 1H), 8.69 (s,1H), 8.15 (s, 1H), 7.73 (s, 1H), 7.63 (d, J = 9.2 Hz, 1H), 7.43 (br d, J= 8.4 Hz, 1H), 6.82 (s, 1H), 5.07-4.86 (m, 1H), 4.28 (q, J = 6.9 Hz,3H), 2.31 (s, 3H), 2.20-2.12 (m, 1H), 1.75-1.63 (m, 1H), 1.46 (t, J =7.0 Hz, 3H), 1.21 (tdd, J = 6.3, 9.0, 12.5 Hz, 1H); LCMS(electrospray)m/z 394.1 (M + H+). H (1S,2S)-N-(6-(7-etho xy-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 288

¹H NMR (400 MHz, DMSO-d₆) δ 13.48 (br s, 1H), 11.21 (s, 1H), 8.71 (s,1H), 8.15 (s, 1H), 7.83 (s, 1H), 7.61 (d, J = 9.2 Hz, 1H), 7.38 (dd, J =1.3, 9.2 Hz, 1H), 5.12-4.79 (m, 1H), 4.31 (q, J = 7.0 Hz, 2H), 2.22 (d,J = 3.1 Hz, 3H), 2.20-2.11 (m, 1H), 1.74-1.60 (m, 1H), 1.39 (t, J = 7.0Hz, 3H), 1.19 (tdd, J = 6.4, 9.1, 12.4 Hz, 1H); LCMS(electrospray) m/z412.1 (M + H+). H (1S,2S)-N-(6-(7-ethoxy-6-fluoro-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA 289

¹H NMR (400 MHz, METHANOL-d₄) δ 8.72 (s, 1H), 7.88-7.81 (m, 2H), 7.79(s, 1H), 7.73 (br d, J = 8.8 Hz, 1H), 6.64-6.55 (m, 1H), 6.49-6.41 (m,1H), 5.87 (br d, J = 11.6 Hz, 1H), 5.07-4.97 (m, 2H), 2.26 (s, 3H),2.19-2.09 (m, 1H), 1.94- 1.81 (m, 1H), 1.35-1.23 (m, 1H);LCMS(electrospray) m/z 419.2 (M + H+). H(1S,2S)-N-(6-(6-acrylamido-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 290

¹H NMR (400 MHz, DMSO-d₆) δ 13.80 (br s, 1H), 11.19 (s, 1H), 8.87 (s,1H), 8.18 (s, 1H), 8.07 (s, 1H), 7.63 (d, J = 9.2 Hz, 1H), 7.46 (dd, J =1.7, 9.2 Hz, 1H), 5.06-4.83 (m, 1H), 3.51-3.50 (m, 2H), 3.08 (t, J = 6.7Hz, 2H), 2.22-2.12 (m, 1H), 1.74- 1.61 (m, 1H), 1.19 (tdd, J = 6.3, 9.1,12.3 Hz, 1H); LCMS(electrospray) m/z 464 (M + H+). H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-((2- hydroxyethyl)thio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 2TFA 291

¹H NMR (400 MHz, DMSO-d₆) δ 11.54-11.33 (m, 1H), 8.73 (br d, J = 3.3 Hz,1H), 8.18 (d, J = 1.6 Hz, 1H), 7.78-7.61 (m, 2H), 7.47 (br t, J = 9.4Hz, 1H), 5.12-4.85 (m, 1H), 2.98 (s, 3H), 2.97 (s, 3H), 2.56 (br d, J =7.3 Hz, 2H), 2.17 (td, J = 6.9, 13.7 Hz, 1H), 1.78-1.59 (m, 1H),1.29-1.21 (m, 1H), 1.10 (t, J = 7.4 Hz, 3H); LCMS(electrospray) m/z425.2 (M + H+). H (1S,2S)-N-(6-(7-(dimethylamino)-5-ethyl-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA 292

¹H NMR (400 MHz, DMSO-d₆) δ 13.45 (br s, 1H), 11.22 (s, 1H), 8.77 (s,1H), 8.16 (s, 1H), 7.90 (s, 1H), 7.63 (d, J = 9.2 Hz, 1H), 7.41 (dd, J =1.5, 9.2 Hz, 1H), 5.06-4.85 (m, 1H), 3.50 (t, J = 6.9 Hz, 2H), 3.02 (t,J = 6.9 Hz, 2H), 2.23 (d, J = 2.9 Hz, 3H), 2.19-2.13 (m, 1H), 1.74-1.60(m, 1H), 1.19 (tdd, J = 6.3, 9.0, 12.3 Hz, 1H); LCMS(electrospray) m/z444 (M + H+). H (1S,2S)-2-fluoro-N-(6-(6-fluoro-7-((2-hydroxyethyl)thio)-5-methyl-1H-indazol- 4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide. 2 TFA 293

¹H NMR (400 MHz, DMSO-d₆) δ 13.89-13.08 (m, 1H), 11.22 (br s, 1H), 8.72(s, 1H), 8.17 (s, 1H), 7.81 (s, 1H), 7.63 (br d, J = 9.1 Hz, 1H), 7.35(br d, J = 9.1 Hz, 1H), 5.07-4.83 (m, 1H), 2.62-2.58 (m, 2H), 2.53 (s,3H), 2.16 (td, J = 6.9, 13.9 Hz, 1H), 1.74-1.60 (m, 1H), 1.24-1.15 (m,1H), 1.10 (t, J = 7.4 Hz, 3H); LCMS(electrospray) m/z 428.3 (M + H+). H(1S,2S)-N-(6-(5-ethyl-6-fluoro-7-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA 294

¹H NMR (400 MHz, CHLOROFORM-d) δ 11.24 (s, 1H), 8.73 (s, 1H), 8.18 (s,1H), 7.75 (s, 1H), 7.64 (d, J = 9.0 Hz, 1H), 7.42 (d, J = 10.4 Hz, 1H),7.36 (br d, J = 9.0 Hz, 1H), 5.12-4.76 (m, 1H), 2.61 (br d, J = 7.3 Hz,2H), 2.23-2.12 (m, 1H), 1.77-1.62 (m, 1H), 1.22-1.16 (m, 1H), 1.10 (t, J= 7.4 Hz, 3H); LCMS(electrospray) m/z 382.3 (M + H+). H(1S,2S)-N-(6-(5-ethyl-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 295

¹H NMR (400 MHz, METHANOL-d₄) δ 8.51 (d, J = 7.2 Hz, 1H), 7.85 (s, 1H),7.66 (s, 1H), 7.00- 6.91 (m, 2H), 5.03-4.96 (m, 1H), 2.16-2.07 (m, 1H),1.89-1.78 (m, 1H), 1.30-1.17 (m, 1H); LCMS(electrospray) m/z 404.1 (M +H+). H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-hydroxy-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA 296

¹H NMR (400 MHz, CHLOROFORM-d) δ 11.23 (s, 1H), 8.77 (s, 1H), 8.17 (s,1H), 7.90 (s, 1H), 7.61 (d, J = 9.0 Hz, 1H), 7.54 (d, J = 9.3 Hz, 1H),7.45 (br d, J = 9.3 Hz, 1H), 5.12-4.81 (m, 1H), 2.25 (s, 3H), 2.21-2.11(m, 1H), 1.75-1.61 (m, 1H), 1.25-1.21 (m, 1H); LCMS(electrospray) m/z400.2 (M + H+). H (1S,2S)-2-fluoro-N-(6-(6-fluoro-5-(methylthio)-1H-indazol-4-yl)imidazo[1,2- a]pyridin-2-yl)cyclopropane-1-carboxamide. 2 TFA 297

¹H NMR (400 MHz, DMSO-d₆) δ 11.17 (s, 1H), 8.75 (d, J = 0.7 Hz, 1H),8.17 (s, 1H), 7.97 (s, 1H), 7.59 (br d, J = 9.2 Hz, 1H), 7.44-7.39 (m,1H), 5.16-4.80 (m, 1H), 2.56-2.54 (m, 3H), 2.38-2.30 (m, 1H), 2.27 (s,3H), 2.21-2.11 (m, 1H), 1.77- 1.62 (m, 1H), 1.25-1.12 (m, 1H);LCMS(electrospray) m/z 446.0 (M + H+). H(1S,2S)-2-fluoro-N-(6-(6-fluoro-5,7- bis(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2- yl)cyclopropane-1-carboxamide. 2 TFA 298

¹H NMR (400 MHz, CHLOROFORM-d) δ 13.00 (s, 1 H), 8.34-8.22 (m, 2 H),7.92 (d, J = 9.17 Hz, 1 H), 7.71-7.61 (m, 2 H), 5.01-4.74 (m, 1 H), 2.67(br d, J = 7.34 Hz, 2 H), 2.20-2.15 (m, 1 H), 2.06-1.96 (m, 2 H),1.33-1.23 (m, 1 H), 1.17 (t, J = 7.46 Hz, 3 H); LCMS(electrospray) m/z400.0 (M + H+). H (1S,2S)-N-(6-(5-ethyl-6,7-difluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 299

¹H NMR (400 MHz, DMSO-d₆) δ 11.16 (s, 1H), 8.74 (s, 1H), 8.18 (s, 1H),7.97 (s, 1H), 7.62 (d, J = 9.2 Hz, 1H), 7.36 (br d, J = 8.9 Hz, 1H),5.09-4.78 (m, 1H), 3.13 (s, 3H), 2.23 (d, J = 2.8 Hz, 3H), 2.20- 2.11(m, 1H), 1.73-1.62 (m, 1H), 1.24-1.12 (m, 1H); LCMS(electrospray) m/z429.11 (M + H+). H (1S,2S)-2-fluoro-N-(6-(6-fluoro-5-methyl-7-(methylsulfinyl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide. 1 TFA 300

¹H NMR (400 MHz, DMSO-d₆) δ 13.42 (br s, 1H), 11.22 (s, 1H), 8.71 (s,1H), 8.16 (s, 1H), 7.86 (s, 1H), 7.60 (d, J = 9.2 Hz, 1H), 7.43 (br d, J= 9.0 Hz, 1H), 5.08-4.85 (m, 1H), 2.99 (d, J = 2.3 Hz, 6H), 2.27 (s,3H), 2.21-2.12 (m, 1H), 1.76-1.61 (m, 1H), 1.26-1.16 (m, 1H);LCMS(electrospray) m/z 443 (M + H+). H(1S,2S)-N-(6-(7-(dimethylamino)-6- fluoro-5-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 1TFA 301

¹H NMR (400 MHz, DMSO-d₆) δ 11.20 (s, 1H), 10.15 (s, 1H), 8.87 (s, 1H),8.19 (s, 1H), 7.98 (s, 1H), 7.64 (d, J = 9.3 Hz, 1H), 7.46 (dd, J = 1.5,9.2 Hz, 1H), 5.08-4.82 (m, 1H), 2.18 (s, 3H), 2.17- 2.11 (m, 1H),1.74-1.62 (m, 1H), 1.26-1.15 (m, 1H); LCMS(electrospray) m/z 445.2 (M +H+). H (1S,2S)-N-(6-(7-acetamido-5-chloro-6-fluoro-1H-indazol-4-yfiimidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 1 TFA 302

¹H NMR (400 MHz, DMSO-d₆) δ 13.38-13.09 (m, 1H), 11.19 (s, 1H), 8.80 (s,1H), 8.19 (s, 1H), 8.03 (s, 1H), 7.64 (d, J = 9.1 Hz, 1H), 7.38 (dd, J =1.6, 9.2 Hz, 1H), 5.09-4.78 (m, 1H), 3.50 (s, 3H), 2.27 (d, J = 2.8 Hz,3H), 2.21-2.12 (m, 1H), 1.74- 1.61 (m, 1H), 1.19 (tdd, J = 6.3, 9.0,12.4 Hz, 1H); LCMS(electrospray) m/z 446.0 (M + H+). H(1S,2S)-2-fluoro-N-(6-(6-fluoro-5-methyl-7-(methylsulfonyl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide. 1 TFA 303

¹H NMR (400 MHz, DMSO-d₆) δ 11.15 (s, 1H), 8.87 (d, J = 0.6 Hz, 1H),8.20 (s, 1H), 8.15 (s, 1H), 7.63 (d, J = 9.3 Hz, 1H), 7.42 (dd, J = 1.7,9.3 Hz, 1H), 5.07-4.82 (m, 1H), 3.19 (s, 3H), 2.21-2.11 (m, 1H),1.74-1.61 (m, 1H), 1.24-1.12 (m, 1H); LCMS(electrospray) m/z 450 (M +H+). H (1S,2S)-N-(6-(5-chloro-6-fluoro-7- (methylsulfinyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 1TFA 304

¹H NMR (400 MHz, DMSO-d₆) δ 11.28 (br s, 1H), 8.77 (s, 1H), 8.17 (s,1H), 8.05 (br d, J = 2.0 Hz, 1H), 7.63 (br d, J = 9.1 Hz, 1H), 7.45 (brd, J = 9.1 Hz, 1H), 5.06-5.02 (m, 1H), 4.89-4.87 (m, 1H), 2.30 (s, 3H),2.21-2.12 (m, 1H), 1.75-1.61 (m, 1H), 1.24-1.13 (m, 1H);LCMS(electrospray) m/z 418 (M + H+). H(1S,2S)-N-(6-(6,7-difluoro-5-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 1 TFA 305

¹H NMR (400 MHz, METHANOL-d₄) δ 8.80 (s, 1H), 7.89-7.86 (m, 2H), 7.77(d, J = 8.9 Hz, 1H), 5.05-4.96 (m, 1H), 4.06 (s, 3H), 2.30 (d, J = 3.1Hz, 3H), 2.13 (ddd, J = 2.3, 4.5, 6.6 Hz, 1H), 1.91- 1.81 (m, 1H),1.31-1.25 (m, 1H); LCMS(electrospray) m/z 426.2 (M + H+). H methyl6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-5-methyl-1H-indazole-7-carboxylate 306

¹H NMR (400 MHz, DMSO-d₆) δ 11.27 (s, 1H), 8.84 (s, 1H), 8.17 (s, 1H),7.95 (s, 1H), 7.65 (d, J = 9.2 Hz, 1H), 7.49 (dd, J = 1.6, 9.2 Hz, 1H),5.04 (dt, J = 3.8, 6.2 Hz, 1H), 4.89-4.85 (m, 1H), 3.27 (q, J = 6.9 Hz,2H), 2.98 (d, J = 2.6 Hz, 3H), 2.20- 2.12 (m, 1H), 1.73-1.63 (m, 1H),1.20 (tdd, J = 6.3, 9.0, 12.4 Hz, 1H), 1.08 (t, J = 7.1 Hz, 3H);LCMS(electrospray) m/z 445.2 (M + H+). H (1S,2S)-N-(6-(5-chloro-7-(ethyl(methyl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 1 TFA 307

¹H NMR (400 MHz, DMSO-d₆) δ 11.14 (s, 1H), 8.68 (s, 1H), 8.13 (s, 1H),7.86 (br d, J = 3.4 Hz, 1H), 7.55 (d, J = 9.2 Hz, 1H), 7.24 (d, J = 9.2Hz, 1H), 5.06-4.79 (m, 1H), 3.02 (d, J = 2.0 Hz, 6H), 2.21-2.11 (m, 1H),1.73-1.61 (m, 1H), 1.21 1.11 (m, 1H); LCMS(electrospray) m/z 465.1 (M +H+). H (1S,2S)-N-(6-(7-(dimethylamino)-6-fluoro-5-(trifluoromethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 308

¹H NMR (400 MHz, DMSO-d₆) δ 13.14-12.81 (m, 1H), 11.30-11.11 (m, 1H),9.94 (s, 1H), 8.75 (s, 1H), 8.16 (s, 1H), 7.80 (s, 1H), 7.66-7.59 (m,1H), 7.43-7.32 (m, 1H), 5.07-4.81 (m, 1H), 2.22 (d, J = 2.9 Hz, 3H),2.16 (s, 4H), 1.74-1.62 (m, 1H), 1.27-1.12 (m, 1H); LCMS(electrospray)m/z 424.15 (M + H+). H (1S,2S)-N-(6-(7-acetamido-6-fluoro-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 1 TFA 309

¹H NMR (400 MHz, DMSO-d₆) δ 13.29 (s, 1H), 11.07 (s, 1H), 8.74 (s, 1H),8.41 (s, 1H), 7.93 (s, 1H), 7.54 (d, J = 9.2 Hz, 1H), 7.29 (d, J = 9.2Hz, 1H), 5.01-4.83 (m, 1H), 3.22 (s, 3H), 2.23-2.16 (m, 1H), 1.78-1.61(m, 1H), 1.23 (br, 9H), 1.28- 1.12 (m, 1H); LCMS (electrospray) m/z532.1 (M + H)+. H tert-butyl 2-(5-chloro-6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-1H-indazol-7-yl)-1-methylhydrazine-1- carboxylate 310

¹H NMR (400 MHz, DMSO-d₆) δ 14.02-13.34 (m, 1H), 11.15 (s, 1H), 8.61 (d,J = 7.0 Hz, 1H), 7.85 (s, 1H), 7.65 (s, 1H), 6.93 (s, 1H), 6.89 (dd, J =1.8, 7.1 Hz, 1H), 5.11-4.78 (m, 1H), 4.35 (q, J = 7.0 Hz, 2H), 2.28 (s,3H), 2.19-2.12 (m, 1H), 1.68 (m, J = 3.2, 6.8, 19.9 Hz, 1H), 1.41 (t, J= 7.0 Hz, 3H), 1.26-1.11 (m, 1H); LCMS(electrospray) m/z 444.2 (M + H+).H (1S,2S)-N-(6-(7-ethoxy-6-fluoro-5-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 1 TFA 311

¹H NMR (400 MHz, DMSO-d₆) δ 10.85 (br s, 1H), 8.70 (s, 1H), 8.15 (s,1H), 7.89 (s, 1H), 7.60 (d, J = 9.0 Hz, 1H), 7.36 (dd, J = 1.5, 9.1 Hz,1H), 5.05- 4.79 (m, 2H), 2.27 (br d, J = 2.6 Hz, 3H), 1.80 (s, 3H),1.77-1.63 (m, 1H), 1.18 (tdd, J = 6.3, 9.2, 12.2 Hz, 1H);LCMS(electrospray) m/z 438.16 (M + H+). H(1S,2S)-2-fluoro-N-(6-(6-fluoro-5-methyl-7-(N-methylacetamido)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide. 1 TFA 312

¹H NMR (400 MHz, METHANOL-d₄) δ 8.78 (s, 1H), 7.91-7.83 (m, 3H),7.80-7.75 (m, 1H), 5.01 (dt, J = 3.9, 6.2 Hz, 1H), 4.13 (br t, J = 6.5Hz, 2H), 3.17 (br t, J = 6.7 Hz, 2H), 2.63 (s, 3H), 2.29 (d, J = 2.9 Hz,3H), 2.17-2.09 (m, 1H), 1.92-1.81 (m, 1H), 1.31-1.26 (m, 1H);LCMS(electrospray) m/z501.3 (M + H+). H 2-((6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1- carboxamido)imidazo[1,2-a]pyridin-6-yl)-5-methyl-1H-indazol-7-yl)thio)ethyl methylcarbamate. 1 TFA 313

¹H NMR (400 MHz, DMSO-d₆) δ 13.19(br s, 1H), 11.16 (s, 1H), 8.79 (s,1H), 8.17 (s, 1H), 7.91 (s, 1H), 7.61 (d, J = 9.0 Hz, 1H), 7.36 (br d, J= 8.9 Hz, 1H), 5.04-4.85(m, 1H), 2.23 (d, J = 3.1 Hz, 3H), 2.19-2.16 (m,1H), 1.72-1.63 (m, 1H), 1.18 (ddd, J = 2.6, 6.2, 9.2 Hz, 1H);LCMS(electrospray) m/z 412.1 (M + H+). H 6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1- carboxamido)imidazo[1,2-a]pyridin-6-yl)-5-methyl-1H-indazole-7-carboxylic acid. 1 TFA 314

¹H NMR (400 MHz, DMSO-d₆) δ 13.49 (br s, 1H), 11.13 (s, 1H), 8.88 (s,1H), 8.19 (s, 1H), 8.08 (s, 1H), 7.61 (d, J = 9.3 Hz, 1H), 7.41 (dd, J =1.8, 9.2 Hz, 1H), 5.06-4.83 (m, 1H), 2.22-2.12 (m, 1H), 1.74-1.57 (m,1H), 1.29-1.06 (m, 1H); LCMS(electrospray) m/z 432.2 (M + H+). H5-chloro-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)- 1H-indazole-7-carboxylic acid.1 TFA 315

¹H NMR (400 MHz, DMSO-d₆) δ 13.69-13.54 (m, 1H), 11.16 (s, 1H), 8.90 (s,1H), 8.20 (s, 1H), 8.13 (s, 1H), 7.63 (br d, J = 9.2 Hz, 1H), 7.44 (brd, J = 9.4 Hz, 1H), 5.12 (d, J = 6.5 Hz, 1H), 4.01 (s, 3H), 2.23-2.11(m, 1H), 1.76-1.61 (m, 1H), 1.28-1.08 (m, 1H); LCMS(electrospray) m/z446.2 (M + H+). H methyl 5-chloro-6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1- carboxamido)imidazo[1,2-a]pyridin-6-yl)-1H-indazole-7-carboxylate. 1 TFA 316

¹H NMR (400 MHz, DMSO-d₆) δ 14.22-13.73 (m, 1H), 11.15 (s, 1H),8.87-8.86 (m, 1H), 8.19 (s, 1H), 8.13 (s, 1H), 7.62 (d, J = 9.3 Hz, 1H),7.47- 7.40 (m, 1H), 5.04-4.84 (m, 1H), 3.23 (s, 3H), 2.17 (ddd, J = 2.0,5.0, 6.9 Hz, 1H), 1.82 (s, 3H), 1.71-1.63 (m, 1H), 1.19-1.13 (m, 1H);LCMS(electrospray) m/z 459.1 (M + H+). H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(N- methylacetamido)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 1TFA 317

¹H NMR (400 MHz, DMSO-d₆) δ 12.93 (s, 1H), 11.06 (s, 1H), 8.70 (s, 1H),8.14 (s, 1H), 7.79 (s, 1H), 7.52 (d, J = 9.2 Hz, 1H), 7.38 (s, 1H), 7.31(d, J = 9.2 Hz, 1H), 5.01-4.83 (m, 1H), 5.01 (s, 1H), 2.60 (s, 3H),2.23-2.16 (m, 1H), 1.78-1.61 (m, 1H), 1.28-1.12 (m, 1H); LCMS(electrospray) m/z 432.1 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(2- methylhydrazineyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 318

¹H NMR (400 MHz, DMSO-d₆) δ 13.60-13.32 (m, 1H), 11.06 (s, 1H), 8.63 (s,1H), 8.15 (s, 1H), 7.74 (s, 1H), 7.54 (d, J = 9.1 Hz, 1H), 7.21 (dd, J =1.6, 9.1 Hz, 1H), 5.04-4.82 (m, 1H), 4.32 (q, J = 7.0 Hz, 2H), 2.60 (brd, J = 6.6 Hz, 2H), 2.20-2.11 (m, 1H), 1.72-1.61 (m, 1H), 1.39 (t, J =6.9 Hz, 3H), 1.20-1.13 (m, 1H), 1.10 (t, J = 7.4 Hz, 3H);LCMS(electrospray) m/z 426.0 (M + H+). H(1S,2S)-N-(6-(7-ethoxy-5-ethyl-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 319

¹H NMR (400 MHz, DMSO-d₆) δ 13.73 (s, 1H), 11.13 (s, 1H), 8.89 (s, 1H),8.22 (s, 1H), 8.10 (s, 1H), 7.62 (d, J = 9.2 Hz, 1H), 7.40 (dd, J = 1.5,9.2 Hz, 1H), 5.08-4.81 (m, 1H), 2.77 (d, J = 6.1 Hz, 3H), 2.25-2.12 (m,1H), 1.76-1.61 (m, 1H), 1.13- 1.19 (m, J = 2.9, 6.1, 12.1 Hz, 1H);LCMS(electrospray) m/z 430.3(M + H+). H(1S,2S)-N-(6-(7-acetyl-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 320

¹H NMR (400 MHz, DMSO-d₆) δ 11.10 (s, 1H), 8.89 (s, 1H), 8.19 (s, 1H),8.06 (s, 1H), 7.60 (d, J = 9.3 Hz, 1H), 7.39 (dd, J = 1.7, 9.3 Hz, 1H),5.10- 4.79 (m, 1H), 3.13 (s, 3H), 2.93 (s, 3H), 2.21-2.12 (m, 1H),1.75-1.60 (m, 1H), 1.08 (s, 1H); LCMS(electrospray) m/z 459.0 (M + H+).H 5-chloro-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-N,N-dimethyl-1H-indazole-7-carboxamide 321

¹H NMR (400 MHz, DMSO-d₆) δ 11.19-11.05 (m, 1H), 8.90-8.81 (m, 1H),8.69-8.61 (m, 1H), 8.49-8.44 (m, 1H) 8.26-8.16 (m, 1H) 8.07-8.00 (m,1H), 7.68-7.54 (m, 1H), 7.42-7.31 (m, 1H), 5.15-4.75 (m, 1H), 2.91 (d, J= 4.2 Hz, 3H), 2.23- 2.11 (m, 1H), 1.76 (br d, J = 4.8 Hz, 1H), 1.27-1.10 (m, 1H); LCMS(electrospray) m/z 445.3 (M + H+). H5-chloro-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-N-methyl-1H-indazole-7-carboxamide 322

¹H NMR (400 MHz, DMSO-d₆) δ 13.43 (s, 1H), 11.10 (s, 1H), 8.77 (s, 1H),8.18 (s, 1H), 7.92 (s, 1H), 7.59 (d, J = 9.2 Hz, 1H), 7.31 (dd, J = 1.6,9.2 Hz, 1H), 5.08-4.79 (m, 1H), 2.74 (d, J = 6.2 Hz, 3H), 2.28 (d, J =3.2 Hz, 3H), 2.16 (td, J = 6.9, 13.9 Hz, 1H), 1.75-1.58 (m, 1H), 1.17(tdd, J = 6.3, 9.1, 12.2 Hz, 1H); LCMS(electrospray) m/z 409.14 (M +H+). H (1S,2S)-N-(6-(7-acetyl-6-fluoro-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 323

¹H NMR (400 MHz, DMSO-d₆) δ 11.21-11.16 (m, 1H), 8.83 (s, 1H), 8.18 (s,1H), 8.15 (br s, 1H), 7.71-7.59 (m, 1H), 7.41 (dd, J = 1.6, 9.2 Hz, 1H),5.06-4.83 (m, 1H), 2.22-2.11 (m, 1H), 1.74-1.59 (m, 1H), 1.19 (tdd, J =6.4, 9.1, 12.4 Hz, 1H); LCMS(electrospray) m/z 406.1 (M + H+). H(1S,2S)-N-(6-(5-chloro-6,7-difluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 324

¹H NMR (400 MHz, DMSO-d₆) δ 13.38 (br s, 1H), 11.06 (s, 1H), 8.66 (s,1H), 8.13 (s, 1H), 7.84 (br s, 1H), 7.51 (d, J = 9.1 Hz, 1H), 7.30 (brd, J = 8.5 Hz, 1H), 5.06-4.81 (m, 1H), 3.25-3.20 (m, 2H), 2.95 (br s,3H), 2.25 (s, 3H), 2.16-2.15 (m, 1H), 1.70-1.63 (m, 1H), 1.19-1.13 (m,1H), 1.07 (t, J = 7.1 Hz, 3H); LCMS(electrospray) m/z 457 (M + H+). H(1S,2S)-N-(6-(7-(ethyl(methyl)amino)-6-fluoro-5-(methylthio)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 325

¹H NMR (400 MHz, DMSO-d₆) δ 13.55 (s, 1H), 11.12 (s, 1H), 8.86 (s, 1H),8.20 (s, 1H), 8.05 (d, J = 16.9 Hz, 3H), 7.61 (d, J = 9.2 Hz, 1H), 7.38(dd, J = 1.6, 9.2 Hz, 1H), 5.11-4.79 (m, 1H), 2.24- 2.08 (m, 1H),1.78-1.57 (m, 1H), 1.21-1.14 (m, 1H); LCMS(electrospray) m/z 431.1 (M +H+). H 5-chloro-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)- 1H-indazole-7-carboxamide 326

¹H NMR (400 MHz, DMSO-d₆) δ 13.16 (br s, 1H), 11.06 (s, 1H), 8.63 (s,1H), 8.14 (s, 1H), 7.68 (s, 1H), 7.53 (d, J = 9.2 Hz, 1H), 7.22 (d, J =9.3 Hz, 1H), 5.06-4.78 (m, 1H), 3.27-3.11 (m, 2H), 2.94 (s, 4H), 2.57(br d, J = 6.8 Hz, 2H), 2.21-2.09 (m, 1H), 1.76-1.58 (m, 1H), 1.25-1.14(m, 1H), 1.11- 1.04 (m, 6H); LCMS(electrospray) m/z 439.2 (M + H+). H(1S,2S)-N-(6-(5-ethyl-7- (ethyl(methyl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 327

¹H NMR (400 MHz, DMSO-d₆) δ 13.52 (br s, 1H), 11.08 (s, 1H), 8.76 (s,1H), 8.13 (s, 1H), 7.93 (s, 1H), 7.58 (d, J = 9.2 Hz, 1H), 7.37 (d, J =9.3 Hz, 1H), 3.00 (d, J = 1.7 Hz, 6H), 2.01-1.90 (m, 1H), 0.92-0.78 (m,4H); LCMS(electrospray) m/z 413.0 (M + H+). HN-(6-(5-chloro-7-(dimethylamino)-6- fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide 328

¹H NMR (400 MHz, DMSO-d₆) δ 13.24 (br s, 1H), 11.07 (s, 1H), 8.84 (s,1H), 8.19 (s, 1H), 8.02 (s, 1H), 7.58-7.54 (m, 1H), 7.50-7.44 (m, 2H),5.04- 4.81 (m, 1H), 3.85 (q, J = 7.0 Hz, 2H), 2.20-2.12 (m, 1H), 1.67(tdd, J = 3.3, 6.8, 20.0 Hz, 1H), 1.21- 1.14 (m, 1H), 1.10 (t, J = 7.0Hz, 3H); LCMS(electrospray) m/z 398.1 (M + H+). H(1S,2S)-N-(6-(5-ethoxy-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 329

¹H NMR (400 MHz, DMSO-d₆) δ 13.41 (br s, 1H), 11.08 (s, 1H), 8.73 (s,1H), 8.16 (s, 1H), 7.88 (s, 1H), 7.57 (d, J = 9.1 Hz, 1H), 7.31 (dd, J =1.4, 9.3 Hz, 1H), 5.08-4.81 (m, 1H), 3.12 (s, 3H), 2.92 (s, 3H), 2.24(d, J = 2.8 Hz, 3H), 2.19-2.11 (m, 1H), 1.72-1.59 (m, 1H), 1.19-1.15 (m,1H); LCMS(electrospray) m/z 439.3 (M + H+). H 6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1- carboxamido)imidazo[1,2-a]pyridin-6-yl)-N,N,5-trimethyl-1H-indazole-7- carboxamide 330

¹H NMR (400 MHz, DMSO-d₆) δ 13.15 (s, 1H), 11.05 (s, 1H), 8.65 (s, 1H),8.13 (s, 1H), 7.76 (s, 1H), 7.53 (d, J = 9.0 Hz, 1H), 7.27 (dd, J = 1.6,9.2 Hz, 1H), 5.07-4.79 (m, 1H), 3.20 (q, J = 6.6 Hz, 2H), 2.92 (s, 3H),2.21-2.12 (m, 4H), 1.73-1.59 (m, 1H), 1.25-1.10 (m, 1H), 1.05 (t, J =7.1 Hz, 3H); LCMS(electrospray) m/z 424.18 (M + H+). H(1S,2S)-N-(6-(7-(ethyl(methyl)amino)-6- fluoro-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 331

¹H NMR (400 MHz, DMSO-d₆) δ 1.12-1.22 (m, 1 H), 1.60-1.73 (m, 1 H),2.12-2.21 (m, 1 H), 4.81- 5.05 (m, 1 H), 7.39 (dd, J = 9.26, 1.75 Hz, 1H), 7.50 (s, 1 H) 7.58-7.64 (m, 1 H), 7.77 (s, 1 H), 8.14 (s, 1 H), 8.19(s, 1 H), 8.87 (s, 1 H), 11.11 (s, 1 H), 13.86-13.91 (m, 1 H);LCMS(electrospray) m/z 438.1 (M + H+). H (1S,2S)-N-(6-(5-chloro-7-(difluoromethyl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 332

¹H NMR (400 MHz, DMSO-d₆) δ 13.49 (br s, 1H), 11.19 (s, 1H), 8.74 (s,1H), 8.11 (s, 1H), 8.00-7.84 (m, 1H), 7.56 (d, J = 9.3 Hz, 1H), 7.33(dd, J = 1.4, 9.2 Hz, 1H), 5.04-4.78 (m, 1H), 3.00 (br s, 6H), 2.46-2.41(m, 1H), 1.61-1.44 (m, 1H), 1.25 (qd, J = 6.6, 13.1 Hz, 1H);LCMS(electrospray) m/z 431.0 (M + H+). H (1R,2S)-N-(6-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 333

¹H NMR (400 MHz, DMSO-d₆) δ 13.99-13.12 (m, 1H), 11.27 (s, 1H), 8.78 (s,1H), 8.13 (s, 1H), 7.93 (s, 1H), 7.60 (d, J = 9.3 Hz, 1H), 7.39 (d, J =9.3 Hz, 1H), 5.05-4.75 (m, 1H), 3.00 (d, J = 2.4 Hz, 6H), 2.44 (br s,1H), 1.63-1.46 (m, 1H), 1.26 (qd, J = 6.4, 13.2 Hz, 1H);LCMS(electrospray) m/z 431.1 (M + H+). H (1S,2R)-N-(6-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 334

¹H NMR (400 MHz, DMSO-d₆) δ 13.77-13.25 (m, 1H), 11.15 (s, 1H), 8.78 (s,1H), 8.17 (s, 1H), 7.94 (s, 1H), 7.59 (d, J = 9.2 Hz, 1H), 7.38 (d, J =9.3 Hz, 1H), 5.09-4.80 (m, 1H), 3.00 (d, J = 2.3 Hz, 6H), 2.16 (td, J =6.8, 13.6 Hz, 1H), 1.73-1.58 (m, 1H), 1.24-1.10 (m, 1H);LCMS(electrospray) m/z 431.1 (M + H+). H (1R,2R)-N-(6-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 335

¹H NMR (400 MHz, DMSO-d₆) δ 13.34 (br s, 1H), 11.05 (s, 1H), 8.93 (s,1H), 8.29 (s, 1H), 8.19 (s, 1H), 7.60-7.56 (m, 1H), 7.55-7.51 (m, 1H),7.15 (d, J = 13.7 Hz, 1H), 5.06-4.80 (m, 1H), 2.95 (d, J = 1.2 Hz, 6H),2.22-2.09 (m, 1H), 1.75-1.59 (m, 1H), 1.16 (br s, 1H);LCMS(electrospray) m/z 397.2 (M + H+). H(1S,2S)-N-(6-(7-(dimethylamino)-6- fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 336

¹H NMR (400 MHz, DMSO-d₆) δ 13.68 (s, 1H), 11.09 (s, 1H), 8.83 (s, 1H),8.18 (s, 1H), 8.08 (s, 1H), 7.59 (d, J = 9.2 Hz, 1H), 7.38 (dd, J = 9.0Hz, J = 1.8 Hz, 1H), 5.03-4.83 (m, 1H), 3.84 (t, J = 6.8 Hz, 2H), 2.52(t, J = 7.4 Hz, 2H), 2.31-2.24 (m, 2H), 2.18-2.13 (m, 1H), 1.71-1.63 (m,1H), 1.23- 1.12 (m, 1H); LCMS (electrospray) m/z 471.1 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(2- oxopyrrolidin-1-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 337

¹H NMR (400 MHz, DMSO-d₆) δ 13.62 (s, 1H), 11.06 (s, 1H), 8.82 (s, 1H),8.16 (s, 1H), 8.11 (br, 1H), 8.08 (s, 1H), 7.59-7.55 (m, 2H), 7.38 (dd,J = 9.0 Hz, J = 1.8 Hz, 1H), 6.73 (d, J = 8.0 Hz, 1H), 6.54 (d, J = 8.0Hz, 1H), 5.03-4.83 (m, 1H), 3.41 (s, 3H), 2.18-2.13 (m, 1H), 1.71-1.63(m, 1H), 1.23-1.12 (m, 1H); LCMS (electrospray) m/z 494.1 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(methyl(pyridin-2-yl)amino)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 338

¹H NMR (400 MHz, DMSO-d₆) δ 13.22 (s, 1H), 11.07 (s, 1H), 8.79-8.65 (m,1H), 8.46-8.34 (m, 1H), 8.17 (s, 1H), 7.90-7.78 (m, 1H), 7.65-7.51 (m,1H), 7.36-7.22 (m, 1H), 5.08-4.78 (m, 1H), 2.89 (br d, J = 4.5 Hz, 3H),2.24 (br d, J = 2.8 Hz, 3H), 2.19-2.13 (m, 1H), 1.74-1.58 (m, 1H), 1.23-1.11 (m, 1H); LCMS(electrospray) m/z 425.1 (M + H+). H6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-N,5-dimethyl-1H-indazole-7-carboxamide 339

¹H NMR (400 MHz, DMSO-d₆) δ 13.67 (br s, 1H), 11.10 (s, 1H), 8.73 (s,1H), 8.18 (s, 1H), 7.97 (s, 1H), 7.60 (d, J = 9.1 Hz, 1H), 7.27 (dd, J =1.6, 9.1 Hz, 1H), 5.05-4.81 (m, 1H), 2.66 (br d, J = 7.3 Hz, 2H),2.22-2.11 (m, 1H), 1.74-1.61 (m, 1H), 1.20-1.14 (m, 1H), 1.10 (t, J =7.4 Hz, 3H); LCMS(electrospray) m/z 450.2 (M + H+). H(1S,2S)-N-(6-(5-ethyl-6-fluoro-7- (trifluoromethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 340

¹H NMR (400 MHz, DMSO-d₆) δ 13.48 (br s, 1H) 11.05 (s, 1 H) 8.94 (s, 1H) 8.36 (br s, 1 H) 8.21 (s, 1 H) 7.52-7.62 (m, 2 H) 7.37 (br d, J =7.25 Hz, 1 H) 7.29 (d, J = 7.50 Hz, 1 H) 4.81-5.04 (m, 1 H) 2.62 (s, 3H) 2.12-2.20 (m, 1 H) 1.61-1.73 (m, 1 H) 1.12-1.23 (m, 1 H);LCMS(electrospray) m/z 382.1 (M + H+). H(1S,2S)-2-fluoro-N-(6-(7-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2- yl)cyclopropane-1-carboxamide 341

¹H NMR (400 MHz, DMSO-d₆) δ 13.70 (s, 1 H), 11.06 (s, 1 H), 8.81 (s, 1H), 8.14(s, 1 H), 8.01 (s, 1 H), 7.54 (s, 1 H), 7.37-7.34 (m, 1 H),4.98-4.80 (m, 1 H), 3.23-3.17 (q, J = 7.0 Hz, 1H), 2.87 (s, 3 H),2.14-2.10 (m, 1 H), 1.66-1.59 (m, 1 H), 1.16-1.10 (m, 1 H), 1.00 (t, J =6.9 Hz, 3 H); LCMS(electrospray) m/z 473.1 (M + H+). H5-chloro-N-ethyl-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-N-methyl-1H-indazole-7-carboxamide 342

¹H NMR (400 MHz, DMSO-d₆) δ 13.63 (s, 1 H) 11.17 (s, 1 H) 9.07 (s, 1 H)8.43(s, 1 H) 8.21 (s, 1 H) 7.72-7.61 (m, 2 H) 7.32 (d, J = 10.4 Hz, 1 H)5.05-4.85 (m, 1 H) 2.51 (s, 3 H) 2.20-2.15 (m, 1 H) 1.72-1.65 (m, 1 H)1.22-1.16 (m, 1 H); LCMS(electrospray) m/z 400.0 (M + H+). H(1S,2S)-2-fluoro-N-(6-(6-fluoro-7-(methylthio)-1H-indazol-4-yl)imidazo[1,2- a]pyridin-2-yl)cyclopropane-1-carboxamide 343

¹H NMR (400 MHz, DMSO-d₆) δ 13.54 (s, 1H), 11.09 (s, 1H), 8.75 (s, 1H),8.16 (s, 1H), 7.94 (d, J = 1.0 Hz, 1H), 7.73-7.43(m, 2H), 7.30 (dd, J =1.6, 9.2 Hz, 1H), 5.10-4.79 (m, 1H), 2.24 (d, J = 2.6 Hz, 3H), 2.19-2.12(m, 1H), 1.74-1.61 (m, 1H), 1.17 (ddd, J = 2.9, 6.2, 12.2 Hz, 1H);LCMS(electrospray) m/z 418.1 (M + H+). H(1S,2S)-N-(6-(7-(difluoromethyl)-6- fluoro-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 344

¹H NMR (400 MHz, DMSO-d₆) δ 14.08 (br s, 1H), 11.11 (s, 1H), 9.05 (s,1H), 8.49 (s, 1H), 8.21 (s, 1H), 7.68-7.63 (m, 1H), 7.61-7.57 (m, 1H),7.48 (d, J = 11.6 Hz, 1H), 5.12-4.84 (m, 1H), 2.25- 2.12 (m, 1H),1.83-1.60 (m, 1H), 1.27-1.08 (m, 1H); LCMS(electrospray) m/z 438.2 (M +H+). H (1S,2S)-2-fluoro-N-(6-(6-fluoro-7-(trifluoromethoxy)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide 345

¹H NMR (400 MHz, DMSO-d₆) δ 13.94 (s, 1H), 11.09 (s, 1H), 8.74 (s, 1H),8.15 (s, 1H), 7.99 (s, 1H), 7.57 (d, J = 9.2 Hz, 1H), 7.31 (dd, J = 1.7,9.2 Hz, 1H), 5.08-4.77 (m, 1H), 2.26 (d, J = 2.8 Hz, 3H), 2.20-2.11 (m,1H), 1.73-1.59 (m, 1H), 1.23- 1.10 (m, 1H); LCMS(electrospray) m/z 452.3(M + H+). H (1S,2S)-2-fluoro-N-(6-(6-fluoro-5-methyl-7-(trifluoromethoxy)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide 346

¹H NMR (400 MHz, DMSO-d₆) δ 13.61 (s, 1H), 11.10 (s, 1H), 8.86 (s, 1H),8.63-8.47 (br, 2H), 8.20 (s, 1H), 8.03 (s, 1H), 7.60 (d, J = 9.6 Hz,1H), 7.43 (t, J = 4.6 Hz, 1H), 6.86 (t, J = 6.0 Hz, 1H), 5.04- 4.83 (m,1H), 3.53 (s, 3H), 2.20-2.13 (m, 1H), 1.72-1.62 (m, 1H), 1.23-1.13 (m,1H); LCMS (electrospray) m/z 495.1 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7- (methyl(pyrimidin-2-yl)amino)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 347

¹H NMR (400 MHz, ACETONE-d₆) δ 13.30 (s, 1H), 10.52 (s, 1H), 9.23 (s,1H), 8.72 (s, 1H), 8.61 (s, 1H), 8.04 (d, J = 9.3 Hz, 1H), 7.90 (d, J =9.1 Hz, 1H), 5.47-5.26 (m, 1H), 4.96-4.73 (m, 2H), 3.75 (s, 3H),2.76-2.71 (m, 1H), 2.33-2.24 (m, 1H), 1.70-1.63 (m, 1H);LCMS(electrospray) m/z 527.1 (M + H+). H5-chloro-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-N-methyl-N-(2,2,2-trifluoroethyl)-1H- indazole-7-carboxamide 348

¹H NMR (400 MHz, DMSO-d₆) δ 13.61 (s, 1H), 11.10 (s, 1H), 8.86 (s, 1H),8.63 (br, 1H), 8.47 (br, 1H), 8.20 (s, 1H), 8.08 (s, 1H), 7.60 (d, J =9.6 Hz, 1H), 7.55 (br, 1H), 7.42 (t, J = 8.0 Hz, 1H), 5.04- 4.83 (m,1H), 3.48 (s, 3H), 2.20-2.15 (m, 1H), 1.72-1.62 (m, 1H), 1.23-1.13 (m,1H); LCMS (electrospray) m/z 495.1 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7- (methyl(pyrimidin-4-yl)amino)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 349

¹H NMR (400 MHz, DMSO-d₆) δ 13.66 (s, 1H), 11.09 (s, 1H), 8.77 (s, 1H),8.59 (s, 1H), 8.46 (s, 1H), 8.20 (s, 1H), 7.96 (s, 1H), 7.82 (d, J = 6.8Hz, 1H), 7.56 (d, J = 8.8 Hz, 1H), 7.34 (t, J = 8.2 Hz, 2H), 5.04-4.83(m, 1H), 4.45 (s, 2H), 2.90 (s, 3H), 2.20-2.15 (m, 1H), 1.72-1.62 (m,1H), 1.23- 1.13 (m, 1H); LCMS (electrospray) m/z 508.1 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7- (methyl(pyridin-3-ylmethyl)amino)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 350

¹H NMR (400 MHz, DMSO-d₆) δ 14.18-13.20 (m, 1H), 11.22 (s, 1H), 8.74 (d,J = 7.2 Hz, 1H), 8.15 (s, 1H), 7.89 (s, 1H), 7.10-6.94 (m, 2H),5.16-4.74 (m, 1H), 4.12 (s, 3H), 2.25-2.09 (m, 1H), 1.78-1.54 (m, 1H),1.29-1.05 (m, 1H); LCMS(electrospray) m/z 470.2 (M + H+). H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1-methyl-1H-tetrazol-5-yl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 351

¹H NMR (400 MHz, DMSO-d₆) δ 14.75-14.36 (m, 1H), 11.13 (s, 1H), 8.90 (s,1H), 8.27 (s, 1H), 8.21 (s, 1H), 7.62 (d, J = 9.2 Hz, 1H), 7.41 (dd, J =1.5, 9.3 Hz, 1H), 5.09-4.80 (m, 1H), 2.22-2.13 (m, 1H), 1.74-1.59 (m,1H), 1.12-1.20 (m, J = 2.9, 6.1, 12.3 Hz, 1H); LCMS(electrospray) m/z413.2 (M + H+). H (1S,2S)-N-(6-(5-chloro-7-cyano-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 352

¹H NMR (400 MHz, DMSO-d₆) δ 13.25-13.17 (m, 1H), 11.02 (s, 1H), 8.84 (s,1H), 8.31-8.24 (m, 1H), 8.18 (s, 1H), 7.57-7.50 (m, 2H), 7.16 (d, J =7.6 Hz, 1H), 6.80 (br d, J = 3.8 Hz, 1H), 5.07-4.78 (m, 1H), 2.92 (br s,6H), 2.23-2.09 (m, 1H), 1.76- 1.58 (m, 1H), 1.27-1.08 (m, 1H);LCMS(electrospray) m/z 379.1 (M + H+). H(1S,2S)-N-(6-(7-(dimethylamino)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 353

¹H NMR (400 MHz, DMSO-d₆) δ 13.69 (s, 1H), 11.08 (s, 1H), 8.76 (s, 1H),8.52 (s, 2H), 8.15 (s, 1H), 7.97 (s, 1H), 7.54 (s, 1H), 7.46 (s, 2H),7.33 (br, 1H), 5.04-4.83 (m, 1H), 4.48 (s, 2H), 2.91 (s, 3H), 2.20-2.15(m, 1H), 1.72-1.62 (m, 1H), 1.23-1.13 (m, 1H); LCMS (electrospray) m/z508.1 (M + H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-(methyl(pyridin-4-ylmethyl)amino)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 354

¹H NMR (400 MHz, DMSO-d₆) δ 13.45 (s, 1H), 11.10 (s, 1H), 8.71 (s, 1H),8.20 (s, 1H), 8.09 (s, 1H), 7.52 (t, J = 9.7 Hz, 2H), 7.28 (td, J = 2.4,8.9 Hz, 1H), 5.05-4.80 (m, 1H), 2.85 (s, 3H), 2.72 (s, 3H), 2.16 (br s,1H), 1.74-1.58 (m, 1H), 1.23-1.12 (m, 1H); LCMS(electrospray) m/z 425.2(M + H+). H 6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-N,N-dimethyl-1H-indazole-7-carboxamide 355

¹H NMR (400 MHz, DMSO-d₆) δ 13.45 (s, 1H), 11.10 (s, 1H), 8.71 (s, 1H),8.20 (s, 1H), 8.09 (s, 1H), 7.52 (t, J = 9.7 Hz, 2H), 7.28 (td, J = 2.4,8.9 Hz, 1H), 5.05-4.80 (m, 1H), 2.85 (s, 3H), 2.72 (s, 3H), 2.16 (br s,1H), 1.74-1.58 (m, 1H), 1.23-1.12 (m, 1H); LCMS(electrospray) m/z 425.2(M + H+). H 6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-N,N-dimethyl-1H-indazole-5-carboxamide 356

¹H NMR (400 MHz, DMSO-d₆) δ 13.98 (s, 1H), 11.08 (s, 1H), 8.81 (s, 1H),8.23-8.18 (m, 2H), 7.55 (d, J = 8.8 Hz, 1H), 7.42 (d, J = 8.8 Hz, 1H),5.03-4.82 (m, 1H), 3.88 (q, J = 7.0 Hz, 2H), 2.17- 2.14 (m, 1H),1.70-1.63 (m, 1H), 1.19-1.16 (m, 1H), 1.10 (t, J = 7.0 Hz, 3H);LCMS(electrospray) m/z 416.1 (M + H+). H(1S,2S)-N-(6-(5-chloro-6-fluoro-7- (trifluoromethoxy)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 357

¹H NMR (400 MHz, DMSO-d₆) δ 13.98 (s, 1H), 11.08 (s, 1H), 8.81 (s, 1H),8.23-8.18 (m, 2H), 7.55 (d, J = 8.8 Hz, 1H), 7.42 (d, J = 8.8 Hz, 1H),5.03-4.82 (m, 1H), 3.88 (q, J = 7.0 Hz, 2H), 2.17- 2.14 (m, 1H),1.70-1.63 (m, 1H), 1.19-1.16 (m, 1H), 1.10 (t, J = 7.0 Hz, 3H);LCMS(electrospray) m/z 416.1 (M + H+). H(1S,2S)-N-(6-(5-ethoxy-6,7-difluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 358

¹H NMR (400 MHz, DMSO-d₆) δ 13.64 (s, 1H), 11.12 (s, 1H), 8.83 (s, 1H),8.18 (s, 1H), 8.03 (s, 1H), 7.59 (d, J = 9.6 Hz, 1H), 7.38 (dd, J = 1.6,9.2 Hz, 1H), 5.03-4.84 (m, 1H), 3.83 (t, J = 7.8 Hz, 2H), 3.60 (t, J =8.0 Hz, 2H), 2.82 (s, 3H), 2.16 (m, 1H), 1.69-1.64 (m, 1H), 1.21-1.15(m, 1H); LCMS (electrospray) m/z 486.10 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(3- methyl-2-oxoimidazolidin-1-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 359

¹H NMR (400 MHz, DMSO-d₆) δ 13.26 (s, 1H), 11.08 (s, 1H), 8.73 (s, 1H),8.14 (s, 1H), 7.90 (s, 1H), 7.53 (d, J = 9.2 Hz, 1H), 7.32 (dd, J = 1.6,9.2 Hz, 1 H), 5.16 (dd, J = 2.6, 9.8 Hz, 1H), 5.03-4.83 (m, 1H), 4.08(s, 1H), 2.19-2.12 (m, 1H), 1.71- 1.61 (m, 1H), 1.22 (d, J = 6.8 Hz,6H), 1.19-1.12 (m, 1H); LCMS (electrospray) m/z 445.10 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7- (isopropylamino)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 360

¹H NMR (400 MHz, DMSO-d₆) δ 13.42 (s, 1H), 11.11 (s, 1H), 8.78 (s, 1H),8.16 (s, 1H), 7.95 (s, 1H), 7.56 (d, J = 9.2 Hz, 1H), 7.36 (dd, J = 1.8,9.4 Hz, 1H), 5.02-4.85 (m, 1H), 3.54 (s, 1H), 2.89 (d, J = 3.2 Hz, 3H),2.19-2.12 (m, 1H), 1.71-1.61 (m, 1H), 1.21-1.13 (m, 7H); LCMS(electrospray) m/z 459.10 (M + H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-(isopropyl(methyl)amino)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 361

¹H NMR (400 MHz, DMSO-d₆) δ 13.40 (s, 1H), 11.10 (s, 1H), 8.77 (s, 1H),8.15 (s, 1H), 7.92 (s, 1H), 7.56 (d, J = 8.8 Hz, 1H), 7.35 (dd, J = 9.2Hz, J = 2.0 Hz, 1H), 5.03-4.83 (m, 1H), 3.01-2.98 (br, 4H), 2.17-2.14(m, 1H), 1.69-1.62 (m, 1H), 1.19-1.14 (m, 1H) 0.64-0.59 (m, 2H),0.48-0.45 (m, 2H); LCMS (electrospray) m/z 457.1 (M + H)+. H(1S,2S)-N-(6-(5-chloro-7- (cyclopropyl(methyl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 362

¹H NMR (400 MHz, DMSO-d₆) δ 13.54 (s, 1H), 11.10 (s, 1H), 8.81 (s, 1H),8.18 (s, 1H), 7.96 (d, J = 1.6 Hz, 1H), 7.58 (d, J = 9.6 Hz, 1H), 7.35(dd, J = 1.6, 9.2 Hz, 1H), 5.47 (t, J = 5.6 Hz, 1H), 5.03- 4.83 (m, 3H),2.19-2.12 (m, 1H), 1.70-1.63 (m, 1H), 1.19-1.12 (m, 1H); LCMS(electrospray) m/z 419.10 (M + H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-(hydroxymethyl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 363

¹H NMR (400 MHz, DMSO-d₆) δ 13.90 (s, 1H), 11.12 (s, 1H), 8.85 (s, 1H),8.18 (s, 1H), 8.07 (d, J = 1.2 Hz, 1H), 7.59 (d, J = 9.6 Hz, 1H), 7.38(dd, J = 2.0, 9.2 Hz, 1H), 5.93 (s, 1H), 5.81 (s, 1H), 5.04- 4.83 (m,1H), 2.19-2.12 (m, 1H), 1.71-1.61 (m, 1H), 1.19-1.13 (m, 1H); LCMS(electrospray) m/z 420.05 (M + H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-(fluoromethyl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 364

¹H NMR (400 MHz, DMSO-d₆) δ 13.73 (s, 1H), 11.15 (s, 1H), 8.93 (s, 1H),8.23 (s, 1H), 8.21 (s, 1H), 7.63 (d, J = 9.2 Hz, 1H), 7.45 (d, J = 9.2Hz, 1H), 5.03-4.84 (m, 1H), 2.55 (s, 3H), 2.16-2.14 (m, 1H), 1.69-1.63(m, 1H), 1.20-1.15 (m, 1H); LCMS (electrospray) m/z 470.10 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(3-methyl-1,2,4-oxadiazol-5-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 365

¹H NMR (400 MHz, DMSO-d₆) δ 13.56-14.07 (1H), 11.12 (s, 1H), 8.84 (d, J= 1.1 Hz, 1H), 8.20 (s, 1H), 8.17 (s, 1H), 7.61 (d, J = 9.3 Hz, 1H),7.39 (dd, J = 9.1, 1.9 Hz, 1H), 7.28 (s, 2H), 6.41 (t, J = 2.2 Hz, 2H),5.04-4.84 (m, 1H), 2.20-2.13 (m, 1H), 1.70-1.64 (m, 1H), 1.20-1.13 (m,1H); LCMS (electrospray) m/z 453.10 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1H-pyrrol-1-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 366

¹H NMR (400 MHz, DMSO-d₆) δ 13.35 (s, 1H), 11.09 (s, 1H), 8.77 (s, 1H),8.14 (s, 1H), 7.97 (s, 1H), 7.54 (d, J = 8.8 Hz, 1H), 7.35 (dd, J = 9.3,1.6 Hz, 1H), 6.79-6.22 (m, 1H), 5.10-4.47 (m, 3H), 2.25-2.09 (m, 1H),1.76-1.57 (m, 1H), 1.21-1.09 (m, 1H); LCMS (electrospray) m/z 442.10(M + H)+. H (1S,2S)-N-(6-(5-chloro-7- ((cyanomethyl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 367

¹H NMR (400 MHz, DMSO-d₆) δ 13.03 (s, 1H), 11.07 (s, 1H), 8.71 (s, 1H),8.16 (d, J = 13.2 Hz, 1H), 7.86 (s, 1H), 7.53 (d, J = 9.3 Hz, 1H), 7.30(dd, J = 8.8, 1.6 Hz, 1H), 6.08 (s, 1H), 5.09-4.81 (m, 1H), 3.12 (s,1H), 2.17-2.08 (m, 1H), 1.66 (d, J = 23.1 Hz, 1H), 1.23-1.14 (m, 1H),0.80 (d, J = 5.5 Hz, 2H), 0.63 (d, J = 3.3 Hz, 2H); LCMS(electrospray)m/z 443.1 (M + H+). H (1S,2S)-N-(6-(5-chloro-7-(cyclopropylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 368

¹H NMR (400 MHz, DMSO-d₆) δ 13.96 (s, 1H), 11.12 (s, 1H), 8.93-8.83 (m,1H), 8.17-8.12 (m, 2H), 7.69-7.57 (m, 1H), 7.46-7.36 (m, 1H), 5.04- 4.83(m, 1H), 3.44 (qd, J = 7.2, 3.7 Hz, 1H), 2.19- 2.12 (m, 1H), 1.71-1.61(m, 1H), 1.23-1.13 (m, 1H), 0.98-0.55 (m, 4H); LCMS(electrospray) m/z539.1 (M + H+). H (1S,2S)-N-(6-(5-chloro-7-(N-cyclopropyl-2,2,2-trifluoroacetamido)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 369

¹H NMR (400 MHz, DMSO-d₆) δ 13.16 (s, 1H), 11.11 (s, 1H), 10.16 (s, 1H),8.83 (d, J = 1.1 Hz, 1H), 8.18 (s, 1H), 7.98 (d, J = 1.6 Hz, 1H), 7.58(d, J = 9.3 Hz, 1H), 7.37 (dd, J = 9.1, 1.9 Hz, 1H), 4.93 (ddd, J =66.2, 9.9, 6.3 Hz, 1H), 4.76 (t, J = 5.5 Hz, 1H), 3.79 (q, J = 6.2 Hz,2H), 2.65 (t, J = 6.6 Hz, 2H), 2.19-2.08 (m, 1H), 1.70-1.61 (m, 1H),1.23- 1.13 (m, 1H); LCMS(electrospray) m/z 475.1 (M + H+). H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(3- hydroxypropanamido)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 370

¹H NMR (400 MHz, DMSO-d₆) δ 13.12-13.48 (1H), 11.08 (s, 1H), 8.72 (s,1H), 8.14 (s, 1H), 7.90 (s, 1H), 7.52 (d, J = 9.3 Hz, 1H), 7.31 (dd, J =9.1, 1.9 Hz, 1H), 5.16 (d, J = 6.9 Hz, 1H), 5.03-4.83 (m, 1H), 3.90 (s,1H), 2.19-2.12 (m, 1H), 1.71- 1.58 (m, 2H), 1.53-1.46 (m, 1H), 1.23-1.12(m, 4H), 0.94 (t, J = 7.4 Hz, 3H); LCMS (electrospray) m/z 459.10 (M +H)+. H (1S,2S)-N-(6-(7-(sec-butylamino)-5- chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 371

¹H NMR (400 MHz, DMSO-d₆) δ 13.38 (s, 1H), 11.10 (s, 1H), 8.77 (d, J =12.6 Hz, 1H), 8.14 (d, J = 8.2 Hz, 1H), 7.97 (s, 1H), 7.54 (t, J = 9.3Hz, 1H), 7.35 (d, J = 9.3 Hz, 1H), 6.66-6.46 (m, 0.5H), 6.11 (d, J = 9.3Hz, 1H), 5.99-5.80 (m, 0.5H), 5.10-4.77 (m, 2H), 2.24-2.09 (m, 1H),1.81-1.58 (m, 4H), 1.21-1.06 (m, 1H); LCMS (electrospray) m/z 456.10(M + H)+. H (1S,2S)-N-(6-(5-chloro-7-((1-cyanoethyl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 372

¹H NMR (400 MHz, DMSO-d₆) δ 13.28 (s, 1H), 11.11 (s, 1H), 8.80 (t, J =1.4 Hz, 1H), 8.18 (s, 1H), 7.94 (d, J = 1.6 Hz, 1H), 7.58 (d, J = 9.3Hz, 1H), 7.35 (dd, J = 9.1, 1.9 Hz, 1H), 5.83 (d, J = 3.8 Hz, 1H),5.43-5.37 (m, 1H), 5.04-4.83 (m, 1H), 2.19- 2.12 (m, 1H), 1.70-1.62 (m,1H), 1.54 (d, J = 6.6 Hz, 3H), 1.23-1.13 (m, 1H); LCMS (electrospray)m/z 433.10 (M + H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1-hydroxyethyl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 373

¹H NMR (400 MHz, DMSO-d₆) δ 13.40 (s, 1H), 11.11 (s, 1H), 8.82 (t, J =1.4 Hz, 1H), 8.17 (s, 1H), 7.99 (s, 1H), 7.61-7.57 (m, 1H), 7.38 (dd, J= 9.3, 1.6 Hz, 1H), 5.07-4.83 (m, 2H), 3.23 (s, 3H), 2.19- 2.12 (m, 1H),1.71-1.61 (m, 1H), 1.57 (t, J = 6.3 Hz, 4H), 1.21-1.13 (m, 2H); LCMS(electrospray) m/z 447.10 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1- methoxyethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 374

¹H NMR (400 MHz, DMSO-d₆) δ 13.68 (s, 1H), 11.11 (s, 1H), 8.83 (t, J =1.4 Hz, 1H), 8.18 (s, 1H), 8.05 (s, 1H), 7.61-7.58 (m, 1H), 7.37 (dd, J= 9.1, 1.9 Hz, 1H), 6.43-6.27 (m, 1H), 5.04-4.83 (m, 1H), 2.20-2.13 (m,1H), 1.83 (dd, J = 23.9, 6.3 Hz, 3H), 1.72-1.61 (m, 1H), 1.21-1.13 (m,1H); LCMS (electrospray) m/z 435.10 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1-fluoroethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 375

¹H NMR (400 MHz, DMSO-d₆) δ 13.37 (s, 1H), 11.44 (s, 1H), 11.11 (s, 1H),8.82 (d, J = 1.1 Hz, 1H), 8.18 (s, 1H), 8.01 (s, 1H), 7.58 (d, J = 9.3Hz, 1H), 7.49 (s, 1H), 7.39 (dd, J = 9.1, 1.9 Hz, 1H), 7.01 (s, 1H),6.68 (s, 1H), 5.04-4.84 (m, 1H), 2.20- 2.13 (m, 1H), 1.71-1-61 (m, 1H),1.23-1.13 (m, 1H); LCMS (electrospray) m/z 454.10 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1H-pyrrol-3-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 376

¹H NMR (400 MHz, DMSO-d₆) δ 13.35 (s, 1H), 11.11 (s, 1H), 8.82 (d, J =1.6 Hz, 1H), 8.18 (s, 1H), 8.01 (s, 1H), 7.58 (d, J = 8.8 Hz, 1H), 7.46(s, 1H), 7.38 (dd, J = 9.1, 1.9 Hz, 1H), 6.96 (s, 1H), 6.64 (s, 1H),5.04-4.83 (m, 1H), 3.75 (s, 3H), 2.20-2.13 (m, 1H), 1.71-1.61 (m, 1H),1.23-1.13 (m, 1H); LCMS (electrospray) m/z 468.10 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1-methyl-1H-pyrrol-3-yl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 377

¹H NMR (400 MHz, DMSO-d₆) δ 13.44 (s, 1H), 11.12 (s, 1H), 8.87 (t, J =1.4 Hz, 1H), 8.19 (s, 1H), 8.04 (s, 1H), 7.60 (d, J = 9.3 Hz, 1H), 7.42(dd, J = 9.1, 1.9 Hz, 1H), 7.08 (s, 1H), 6.39-6.37 (m, 1H), 6.26 (t, J =3.0 Hz, 1H), 5.04-4.84 (m, 1H), 3.54 (d, J = 1.1 Hz, 3H), 2.20-2.13 (m,1H), 1.72-1.62 (m, 1H), 1.23-1.13 (m, 1H); LCMS (electrospray) m/z468.10 (M + H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1-methyl-1H-pyrrol-2-yl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 378

¹H NMR (400 MHz, DMSO-d₆) δ 13.57 (s, 1H), 11.12 (s, 1H), 8.88 (t, J =1.1 Hz, 1H), 8.21 (s, 1H), 8.10 (s, 1H), 7.70 (d, J = 1.6 Hz, 1H), 7.62(d, J = 9.3 Hz, 1H), 7.43 (dd, J = 9.1, 1.9 Hz, 1H), 6.64 (d, J = 1.4Hz, 1H), 5.04-4.84 (m, 1H), 3.76 (s, 3H), 2.20-2.13 (m, 1H), 1.71-1.62(m, 1H), 1.23-1.13 (m, 1H); LCMS (electrospray) m/z 469.10 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1-methyl-1H-pyrazol-5-yl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 379

¹H NMR (400 MHz, DMSO-d₆) δ 13.94 (s, 1H), 11.11 (s, 1H), 9.01 (s, 1H),8.86 (s, 1H), 8.17 (s, 1H), 8.09 (s, 1H), 7.59 (d, J = 9.1 Hz, 1H), 7.39(dd, J = 9.2, 1.5 Hz, 1H), 6.36 (s, 2H), 5.02-4.85 (m, 1H), 2.18-2.14(m, 1H), 1.70-1.63 (m, 1H), 1.20-1.14 (m, 1H); LCMS (electrospray) m/z470.10 (M + H)+. I (1S,2S)-N-(6-(7-((2H-tetrazol-2-yl)methyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 380

¹H NMR (400 MHz, DMSO-d₆) δ 13.56 (s, 1H), 11.10 (s, 1H), 8.82 (d, J =1.1 Hz, 1H), 8.17 (s, 1H), 7.96 (s, 1H), 7.57 (d, J = 9.3 Hz, 1H), 7.36(dd, J = 9.1, 1.9 Hz, 1H), 5.04-4.83 (m, 1H), 3.91 (d, J = 1.1 Hz, 2H),3.20 (q, J = 6.8 Hz, 4H), 2.19-2.12 (m, 1H), 2.00-1.93 (m, 2H),1.71-1.61 (m, 1H), 1.23- 1.13 (m, 1H); LCMS (electrospray) m/z 457.10(M + H)+. H (1S,2S)-N-(6-(7-(azetidin-1-ylmethyl)-5-chloro-6-fluoro-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 381

¹H NMR (400 MHz, DMSO-d₆) δ 13.50 (s, 1H), 11.11 (s, 1H), 8.82 (d, J =1.1 Hz, 1H), 8.18 (s, 1H), 7.98 (s, 1H), 7.58 (d, J = 9.3 Hz, 1H), 7.37(dd, J = 9.3, 1.6 Hz, 1H), 5.04-4.84 (m, 1H), 4.00 (d, J = 1.1 Hz, 2H),2.53-2.49 (m, 4H), 2.20-2.13 (m, 1H), 1.70-1.62 (m, 5H), 1.24-1.13 (m,1H); LCMS (electrospray) m/z 472.10 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7- (pyrrolidin-1-ylmethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 382

¹H NMR (400 MHz, DMSO-d₆) δ 13.41 (s, 1H), 11.11 (s, 1H), 8.83 (t, J =1.1 Hz, 1H), 8.17 (s, 1H), 7.97 (s, 1H), 7.58 (d, J = 9.3 Hz, 1H), 7.38(dd, J = 9.1, 1.9 Hz, 1H), 5.04-4.83 (m, 1H), 3.84 (s, 2H), 2.44 (s,4H), 2.19-2.12 (m, 1H), 1.70-1.62 (m, 1H), 1.51-1.37 (m, 6H), 1.23-1.13(m, 1H); LCMS (electrospray) m/z 486.10 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7- (piperidin-1-ylmethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 383

¹H NMR (400 MHz, DMSO-d₆) δ 13.92 (s, 1H), 11.11 (s, 1H), 8.85 (d, J =1.1 Hz, 1H), 8.17 (s, 1H), 8.07 (s, 1H), 7.81 (s, 2H), 7.58 (d, J = 9.3Hz, 1H), 7.38 (dd, J = 9.1, 1.9 Hz, 1H), 6.07 (s, 2H), 5.04- 4.83 (m,1H), 2.19-2.12 (m, 1H), 1.71-1.61 (m, 1H), 1.21-1.13 (m, 1H); LCMS(electrospray) m/z 469.10 (M + H)+. I(1S,2S)-N-(6-(7-((2H-1,2,3-triazol-2-yl)methyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 384

¹H NMR (400 MHz, DMSO-d₆) δ 13.95 (s, 1H), 11.11 (s, 1H), 8.83 (t, J =1.4 Hz, 1H), 8.31 (d, J = 1.4 Hz, 1H), 8.17 (s, 1H), 8.09 (s, 1H), 7.75(d, J = 1.1 Hz, 1H), 7.58 (d, J = 9.3 Hz, 1H), 7.37 (dd, J = 9.1, 1.9Hz, 1H), 6.03 (s, 2H), 5.04-4.83 (m, 1H), 2.19-2.12 (m, 1H), 1.71-1.61(m, 1H), 1.21-1.13 (m, 1H); LCMS (electrospray) m/z 469.10 (M + H)+. I(1S,2S)-N-(6-(7-((1H-1,2,3-triazol-1-yl)methyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 385

¹H NMR (400 MHz, DMSO-d₆) δ 13.92 (s, 1H), 11.11 (s, 1H), 8.83 (d, J =1.1 Hz, 1H), 8.79 (s, 1H), 8.16 (s, 1H), 8.07 (s, 1H), 7.96 (s, 1H),7.58 (d, J = 9.3 Hz, 1H), 7.37 (dd, J = 9.1, 1.9 Hz, 1H), 5.83 (s, 2H),5.04-4.83 (m, 1H), 2.19-2.12 (m, 1H), 1.71- 1.61 (m, 1H), 1.21-1.13 (m,1H); LCMS (electrospray) m/z 469.10 (M + H)+. I(1S,2S)-N-(6-(7-((1H-1,2,4-triazol-1-yl)methyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 386

¹H NMR (400 MHz, DMSO-d₆) δ 13.86 (s, 1H), 11.12 (s, 1H), 8.85 (s, 1H),8.17 (s, 1H), 8.08 (s, 1H), 7.58 (d, J = 9.6 Hz, 1H), 7.38 (dd, J = 9.3,1.6 Hz, 1H), 7.33 (d, J = 1.1 Hz, 1H), 6.93-6.91 (m, 1H), 5.04-4.83 (m,1H), 3.80 (d, J = 15.4 Hz, 3H), 2.19-2.12 (m, 1H), 1.70-1.62 (m, 1H),1.23-1.13 (m, 1H); LCMS (electrospray) m/z 501.10 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-((1- methyl-1H-imidazol-2-yl)thio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 387

¹H NMR (400 MHz, DMSO-d₆) δ 13.20-13.84 (s, 1 H) 8.84 (s, 1 H) 8.71 (d,J = 9.4 Hz, 1 H) 7.92 (s, 1 H) 7.87 (s, 1 H) 7.49 (d, J = 9.13 Hz, 1 H)7.27 (dd, J = 9.26, 1.75 Hz, 1 H) 6.87 (br s, 1 H) 3.00 (d, J = 2.38 Hz,6 H) 2.66-2.70 (m, 1 H) 0.61-0.71 (m, 2 H) 0.39-0.46 (m, 2 H); LCMS(electrospray) m/z 428.1 (M + H+). H 1-(6-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2- a]pyridin-2-yl)-3-cyclopropylurea388

¹H NMR (400 MHz, DMSO-d₆) δ 11.12 (s, 1H), 8.89 (s, 1H), 8.21 (s, 1H),8.15 (s, 1H), 7.62 (d, J = 9.2 Hz, 1H), 7.44 (dd, J = 1.6, 9.3 Hz, 1H),6.95 (br s, 1H), 6.27 (t, J = 3.1 Hz, 1H), 6.14 (br s, 1H), 5.13-4.80(m, 1H), 2.18 (td, J = 7.0, 13.9 Hz, 1H), 2.07 (s, 3H), 1.74-1.61 (m,1H), 1.23-1.13 (m, 1H); LCMS (electrospray) m/z 467.1 (M + H+). H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(2-methyl-1H-pyrrol-1-yl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 389

¹H NMR (400 MHz, DMSO-d₆) δ 13.70-11.96 (m, 1H), 11.08 (s, 1H), 8.79 (s,1H), 8.17 (s, 1H), 7.89 (s, 1H), 7.57 (d, J = 9.2 Hz, 1H), 7.35 (dd, J =1.7, 9.2 Hz, 1H), 6.56-5.57 (m, 1H), 5.21-4.65 (m, 1H), 2.25-2.09 (m,1H), 1.69 (d, J = 1.4 Hz, 6H), 1.65-1.59 (m, 1H), 1.17 (tdd, J = 6.3,9.1, 12.3 Hz, 1H); LCMS (electrospray) m/z 446.0 (M + H+). H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(2- hydroxypropan-2-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 390

¹H NMR (400 MHz, DMSO-d₆) δ 13.66 (s, 1H), 11.11 (s, 1H), 8.83 (s, 1H),8.18 (s, 1H), 8.00 (d, J = 1.1 Hz, 1H), 7.59 (d, J = 9.3 Hz, 1H), 7.37(dd, J = 9.1, 1.9 Hz, 1H), 5.04-4.83 (m, 3H), 3.36 (s, 3H), 2.19-2.12(m, 1H), 1.71-1.61 (m, 1H), 1.23-1.13 (m, 1H); LCMS (electrospray) m/z432.10 (M + H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-(methoxymethyl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 391

¹H NMR (400 MHz, DMSO-d₆) δ 13.65 (s, 1H), 11.11 (s, 1H), 8.83 (d, J =1.1 Hz, 1H), 8.18 (s, 1H), 8.00 (d, J = 1.6 Hz, 1H), 7.59 (d, J = 9.3Hz, 1H), 7.37 (dd, J = 9.3, 1.6 Hz, 1H), 5.04-4.83 (m, 3H), 3.57 (q, J =7.1 Hz, 2H), 2.19-2.12 (m, 1H), 1.66 (dtd, J = 23.3, 6.7, 3.5 Hz, 1H),1.39 (s, 0H), 1.24- 1.13 (m, 4H); LCMS (electrospray) m/z 446.10 (M +H)+. H (1S,2S)-N-(6-(5-chloro-7-(ethoxymethyl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 392

¹H NMR (400 MHz, DMSO-d₆) δ 13.76-14.21 (1H), 11.11 (s, 1H), 9.64 (s,1H), 8.84 (s, 1H), 8.17 (s, 1H), 8.09 (s, 1H), 7.59 (d, J = 9.3 Hz, 1H),7.38 (d, J = 8.8 Hz, 1H), 6.11 (s, 2H), 5.01-4.85 (m, 1H), 2.19-2.12 (m,1H), 1.69-1.63 (m, 1H), 1.19- 1.13 (m, 1H); LCMS (electrospray) m/z470.10 (M + H)+. I (1S,2S)-N-(6-(7-((1-tetrazol-1-yl)methyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 393

¹H NMR (400 MHz, DMSO-d₆) δ 13.54-13.94 (s, 1H), 11.06 (d, J = 7.7 Hz,1H), 8.98 (d, J = 11.5 Hz, 1H), 8.80 (s, 1H), 8.12 (s, 2H), 7.58-7.54(m, 1H), 7.35 (dd, J = 9.3, 1.6 Hz, 1H), 6.74 (q, J = 7.1 Hz, 1H),5.00-4.79 (m, 1H), 2.24-2.20 (m, 3H), 2.16- 2.09 (m, 1H), 1.68-1.57 (m,1H), 1.18-1.09 (m, 1H); LCMS (electrospray) m/z 485.10 (M + H)+. I(1S,2S)-N-(6-(7-(1-(2H-tetrazol-2-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 394

¹H NMR (400 MHz, DMSO-d₆) δ 13.42 (s, 1H), 11.06 (d, J = 6.6 Hz, 1H),8.71 (d, J = 7.7 Hz, 1H), 8.13 (d, J = 7.7 Hz, 1H), 7.88 (d, J = 1.1 Hz,1H), 7.52 (t, J = 8.5 Hz, 1H), 7.31 (dd, J = 9.3, 1.6 Hz, 1H), 5.56-5.52(m, 1H), 5.03-4.82 (m, 2H), 3.09 (s, 3H), 2.85 (s, 3H), 2.19-2.12 (m,1H), 1.71-1.61 (m, 1H), 1.34 (d, J = 6.6 Hz, 3H), 1.21-1.12 (m, 1H);LCMS (electrospray) m/z 503.15 (M + H)+. H (1S,2S)-N-(6-(5-chloro-7-((1-(dimethylamino)-1-oxopropan-2- yl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 395

¹H NMR (400 MHz, DMSO-d₆) δ13.01 (s, 1H), 11.09 (s, 1H), 8.81 (s, 1H),8.16 (s, 1H), 7.94 (s, 1H), 7.58 (d, J = 9.3 Hz, 1H), 7.37 (dd, J = 1.7,9.3 Hz, 1H), 5.08-4.80 (m, 1H), 3.18 (s, 3H), 2.15 (br d, J = 7.0 Hz,1H), 1.71 (br d, J = 2.7 Hz, 6H), 1.64 (br s, 1H), 1.17 (br dd, J = 8.9,12.1 Hz, 1H); LCMS (electrospray) m/z 460.2 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(2- methoxypropan-2-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 396

¹H NMR (400 MHz, DMSO-d₆) δ 13.37-12.98 (m, 1H), 11.09 (s, 1H), 8.82 (s,1H), 8.22 (s, 1H), 8.16 (s, 1H), 7.95 (s, 1H), 7.57 (d, J = 9.2 Hz, 1H),7.37 (dd, J = 1.7, 9.2 Hz, 1H), 5.03-4.82 (m, 1H), 3.87 (q, J = 6.6 Hz,1H), 2.21 (s, 6H), 2.16 (br dd, J = 6.1, 7.6 Hz, 1H), 1.72-1.61 (m, 1H),1.49 (d, J = 6.8 Hz, 3H), 1.23-1.13 (m, 1H); LCMS (electrospray) m/z459.2 (M + H)+. H (1S,2S)-N-(6-(5-chloro-7-(1-(dimethylamino)ethyl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. Formaic acid salt 397

¹H NMR (400 MHz, DMSO-d₆) δ 13.26-13.88 (1H), 11.08 (s, 1H), 8.71 (d, J= 1.6 Hz, 1H), 8.15 (s, 1H), 7.94 (s, 1H), 7.53 (d, J = 9.3 Hz, 1H),7.30 (dd, J = 9.3, 1.6 Hz, 1H), 5.75 (d, J = 3.3 Hz, 1H), 5.03-4.83 (m,1H), 4.42 (d, J = 4.4 Hz, 2H), 3.02 (s, 3H), 2.88 (s, 3H), 2.19-2.12 (m,1H), 1.71-1.61 (m, 1H), 1.23-1.12 (m, 1H); LCMS (electrospray) m/z 488.1(M + H)+. H (1S,2S)-N-(6-(5-chloro-7-((2-(dimethylamino)-2-oxoethyl)amino)-6- fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 398

¹H NMR (400 MHz, DMSO-d₆) δ 13.53-14.00 (1H), 11.12 (s, 1H), 9.77 (s,1H), 8.83 (s, 1H), 8.20- 8.17 (m, 2H), 7.59 (d, J = 9.1 Hz, 1H), 7.38(dd, J = 9.3, 1.6 Hz, 1H), 6.59 (q, J = 7.1 Hz, 1H), 5.04- 4.83 (m, 1H),2.21 (d, J = 7.1 Hz, 3H), 2.17-2.12 (m, 1H), 1.70-1.63 (m, 1H),1.20-1.13 (m, 1H); LCMS (electrospray) m/z 484.10 (M + H)+. I(1S,2S)-N-(6-(7-(1-(1H-tetrazol-1-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 399

¹H NMR (400 MHz, DMSO-d₆) δ 11.10 (s, 1H), 8.79 (s, 1H), 8.20 (d, J =15.8 Hz, 2H), 8.00 (s, 1H), 7.58 (d, J = 9.2 Hz, 1H), 7.34 (dd, J = 1.8,9.2 Hz, 1H), 5.03-4.84 (m, 1H), 4.81-4.75 (m, 1H), 2.22- 2.09 (m, 1H),1.75-1.59 (m, 1H), 1.54 (d, J = 6.8 Hz, 3H), 1.27-1.12 (m, 1H); LCMS(electrospray) m/z 431.1 (M + H)+. H(1S,2S)-N-(6-(7-(1-aminoethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 400

¹H NMR (400 MHz, DMSO-d₆) δ 14.12-13.82 (m, 1H), 11.11 (s, 1H), 8.84 (s,1H), 8.27-8.14 (m, 1H), 7.64 (s, 1H), 7.61 (d, J = 9.2 Hz, 1H), 7.39(dd, J = 9.1, 1.8 Hz, 1H), 7.27 (s, 1H), 6.66 (dd, J = 2.9, 1.6 Hz, 1H)5.10-4.79 (m, 1H), 3.22-3.00 (m, 6H), 2.21-2.12 (m, 1H), 1.74-1.61(m,1H), 1.24-1.12 (m, 1H); LCMS (electrospray) m/z 524.1 (M + H)+. H1-(5-chloro-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-1H-indazol-7-yl)-N,N-dimethyl-1H- pyrrole-3-carboxamide 401

¹H NMR (400 MHz, DMSO-d₆) δ 13.79 (s, 1 H) 11.18 (s, 1 H) 8.67 (d, J =7.09 Hz, 1 H) 7.93 (s, 1 H) 7.77 (s, 1 H) 6.92-6.99 (m, 2 H) 4.82-5.08(m, 1 H) 4.53 (s, 1 H) 2.15 (m, 1 H) 1.61-1.75 (m, 1 H) 1.12-1.27 (m, 1H) 0.92 (br s, 2 H) 0.68- 0.77 (m, 2 H); LCMS (electrospray) m/z 444.0(M + H)+. H (1S,2S)-N-(6-(5-chloro-7-cyclopropoxy-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 402

¹H NMR (400 MHz, DMSO-d₆) δ 11.08 (s, 1H), 8.81 (s, 1H), 8.27 (br s,1H), 8.16 (s, 1H), 7.96 (s, 1H), 7.57 (d, J = 9.3 Hz, 1H), 7.37 (dd, J =1.7, 9.3 Hz, 1H), 5.12-4.75 (m, 1H), 4.33 (d, J = 6.8 Hz, 1H), 2.22-2.12(m, 4H), 1.74-1.59 (m, 1H), 1.47 (d, J = 6.7 Hz, 3H), 1.22-1.12 (m, 1H);LCMS (electrospray) m/z 445.2 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1- (methylamino)ethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 403

¹H NMR (400 MHz, DMSO-d₆) δ 13.35-13.11 (m, 1H), 10.33 (s, 1H), 8.40 (s,1H), 7.96-7.72 (m, 1H), 7.44 (s, 2H), 6.36 (d, J = 1.4 Hz, 1H), 5.79 (s,2H), 5.09 (dd, J = 2.4, 9.4 Hz, 1H), 5.05-4.81 (m, 1H), 4.17-3.92 (m,1H), 4.14-2.74 (m, 1H), 2.17- 2.05 (m, 1H), 1.71-1.55 (m,12H), 1.23 (d,J = 6.3 Hz, 6H), 1.21-1.08 (m, 1H); LCMS (electrospray) m/z 460.2 (M +H)+. H (1S,2S)-N-(8-amino-6-(5-chloro-6-fluoro-7-(isopropylamino)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 1 formic acid 404

¹H NMR (400 MHz, DMSO-d₆) δ 14.17-13.33 (m, 1H), 11.08 (s, 1H), 8.79 (s,1H), 8.16 (s, 1H), 8.00 (s, 1H), 7.56 (d, J = 9.3 Hz, 1H), 7.35 (dd, J =1.5, 9.2 Hz, 1H), 5.06-4.81 (m, 1H), 4.73 (br d, J = 1.1 Hz, 1H), 2.16(td, J = 6.9, 13.8 Hz, 1H), 2.07 (s, 1H), 1.76-1.56 (m, 1H), 1.37 (d, J= 6.0 Hz, 6H), 1.17 (tdd, J = 6.2, 9.0, 12.3 Hz, 1H); LCMS(electrospray) m/z 446.1 (M + H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-isopropoxy-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 405

¹H NMR (400 MHz, DMSO-d₆) δ 13.55 (br s, 1H), 11.08 (s, 1H), 8.78 (d, J= 1.0 Hz, 1H), 8.16 (s, 1H), 7.96 (s, 1H), 7.57 (d, J = 9.3 Hz, 1H),7.35 (dd, J = 1.8, 9.3 Hz, 1H), 5.05-4.80 (m, 1H), 3.67-3.55 (m, 1H),2.16 (td, J = 7.0, 14.0 Hz, 1H), 1.73-1.59 (m, 1H), 1.45 (d, J = 7.0 Hz,6H), 1.17 (tdd, J = 6.1, 9.1, 12.1 Hz, 1H); LCMS (electrospray) m/z430.2 (M + H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-isopropyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 406

¹H NMR (400 MHz, DMSO-d₆) δ 13.54 (s, 1H), 11.11 (s, 1H), 8.79 (s, 1H),8.17 (s, 1H), 7.96 (d, J = 1.1 Hz, 1H), 7.57 (d, J = 9.3 Hz, 1H), 7.35(dd, J = 9.3, 1.6 Hz, 1H), 5.04-4.83 (m, 1H), 3.61 (q, J = 8.8 Hz, 1H),2.19-1.91 (m, 8H), 1.73-1.61 (m, 3H), 1.24-1.07 (m, 1H); LCMS(electrospray) m/z 456.10 (M + H)+. H(1S,2S)-N-(6-(5-chloro-7-cyclopentyl-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 407

¹H NMR (400 MHz, DMSO-d₆) δ 14.18-13.49 (m, 1H), 11.09 (s, 1H), 9.02 (s,1H), 8.83 (s, 1H), 8.28-7.99 (m, 2H), 7.58 (d, J = 9.2 Hz, 1H), 7.38(dd, J = 1.7, 9.2 Hz, 1H), 6.78 (q, J = 6.9 Hz, 1H), 5.10-4.74 (m, 1H),2.27 (d, J = 7.0 Hz, 3H), 2.21- 2.11 (m, 1H), 1.74-1.59 (m, 1H),1.22-1.12 (m, 1H); LCMS (electrospray) m/z 484.1 (M + H)+. I(1S,2S)-N-(6-(7-((R)-1-(2H-tetrazol-2-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 408

¹H NMR (400 MHz, DMSO-d₆) δ 14.19-13.48 (m, 1H), 11.09 (s, 1H), 9.02 (s,1H), 8.83 (s, 1H), 8.31-7.98 (m, 2H), 7.59 (d, J = 9.2 Hz, 1H), 7.38(dd, J = 1.7, 9.2 Hz, 1H), 6.78 (q, J = 7.1 Hz, 1H), 5.09-4.68 (m, 1H),2.27 (d, J = 7.0 Hz, 3H), 2.20- 2.10 (m, 1H), 1.67 (tdd, J = 3.2, 6.8,19.9 Hz, 1H), 1.23-1.13 (m, 1H); LCMS (electrospray) m/z 484.1 (M + H)+.I (1S,2S)-N-(6-(7-((S)-1-(2H-tetrazol-2-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 409

¹H NMR (400 MHz, DMSO-d₆) δ 13.38 (s, 1H), 11.10 (s, 1H), 8.86 (s, 1H),8.17 (s, 1H), 8.01 (d, J = 1.6 Hz, 1H), 7.59 (q, J = 9.7 Hz, 2H), 7.40(dd, J = 9.3, 1.6 Hz, 1H), 5.82-5.75 (m, 1H), 5.04-4.83 (m, 1H),2.20-2.13 (m, 1H), 1.72-1.62 (m, 1H), 1.28-1.11 (m, 1H); LCMS(electrospray) m/z 487.1 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(2,2,2-trifluoro-1-hydroxyethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 410

¹H NMR (400 MHz, DMSO-d₆) δ 13.51 (s, 1H), 11.08 (s, 1H), 8.77 (s, 1H),8.18 (s, 1H), 7.95 (s, 1H), 7.57 (d, J = 9.3 Hz, 1H), 7.34 (dd, J = 9.3,1.6 Hz, 1H), 5.03-4.83 (m, 2H), 4.50-4.42 (m, 3H), 3.51-3.38 (m, 6H),2.20-2.07 (m, 3H), 1.99-1.83 (m, 3H), 1.72-1.61 (m, 2H), 1.23-1.13 (m,4H); LCMS (electrospray) m/z 472.10 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(2- hydroxycyclopentyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 411

¹H NMR (400 MHz, DMSO-d₆) δ 8.62-8.72 (m, 1 H) 8.12-8.25 (m, 1 H)7.83-7.96 (m, 1 H) 7.56- 7.62 (m, 1 H) 7.43-7.52 (m, 1 H) 4.95-4.98 (m,0.5 H) 4.77-4.81 (m, 0.5 H) 2.70-2.80 (m, 3 H) 2.07-2.17 (m, 1H)1.73-1.88 (m, 1 H) 1.18-1.31 (m, 1 H); LCMS (electrospray) m/z 461.3(M + H)+. H (1S,2S)-N-(6-(5-chloro-7-ethanethioamido-6-fluoro-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 412

¹H NMR (400 MHz, DMSO-d₆) δ 13.54-12.76 (m, 1H), 11.09 (s, 1H), 8.80 (s,1H), 8.36 (s, 1H), 8.17 (s, 1H), 8.07-7.97 (m, 1H), 7.58 (d, J = 9.2 Hz,1H), 7.36 (br d, J = 9.0 Hz, 1H), 7.23 (br d, J = 6.8 Hz, 1H), 6.87 (brd, J = 5.0 Hz, 1H), 6.07 (q, J = 6.7 Hz, 1H), 5.82-5.67 (m, 1H),5.13-4.80 (m, 1H), 3.02 (s, 3H), 2.78 (br s, 1H), 2.20-2.14 (m, 1H),2.10-2.00 (m, 3H), 1.86-1.75 (m, 1H), 1.71- 1.64 (m, 3H), 1.28-1.07 (m,1H); LCMS (electrospray) m/z 487.1 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1-(N-methylacetamido)ethyl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 413

¹H NMR (400 MHz, DMSO-d₆) δ 11.10 (s, 1H), 9.77 (s, 1H), 8.82 (s, 1H),8.24-8.00 (m, 2H), 7.58 (d, J = 9.1 Hz, 1H), 7.37 (dd, J = 1.6, 9.3 Hz,1H), 6.62 (d, J = 7.4 Hz, 1H), 5.11-4.74 (m, 1H), 2.25- 2.15 (m, 4H),1.79-1.56 (m, 1H), 1.27-1.10 (m, 1H); LCMS (electrospray) m/z 484.1 (M +H)+. I (1S,2S)-N-(6-7-((R)-1-(1H-tetrazol-1-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 414

¹H NMR (400 MHz, DMSO-d₆) δ 13.75 (br s, 1H), 11.09 (s, 1H), 9.75 (s,1H), 8.82 (s, 1H), 8.17 (s, 1H), 8.08 (s, 1H), 7.59 (br d, J = 8.9 Hz,1H), 7.37 (dd, J = 1.7, 9.2 Hz, 1H), 6.59 (br d, J = 6.8 Hz, 1H),5.12-4.75 (m, 1H), 2.26-2.07 (m, 4H), 1.75- 1.60 (m, 1H), 1.21-1.15 (m,1H); LCMS (electrospray) m/z 484.1 (M + H)+. I(1S,2S)-N-(6-(7-((S)-1-(1H-tetrazol-1-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 415

¹H NMR (400 MHz, DMSO-d₆) δ 13.40-13.49 (1H), 11.06-11.17 (1H),8.83-8.91 (1H), 8.15-8.21 (1H), 8.02-8.09 (1H), 7.57-7.64 (1H),7.38-7.46 (1H), 5.72-5.82 (1H), 4.82-5.07 (1H), 3.46-3.55 (3H),2.12-2.21 (1H), 1.61-1.74 (1H), 1.13-1.22 (1H); LCMS (electrospray) m/z501.1 (M + H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-(2,2,2-trifluoro-1-methoxyethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 416

¹H NMR (400 MHz, DMSO-d₆) δ 13.23 (s, 1H), 11.06 (s, 1H), 8.72 (s, 1H),8.16 (s, 1H), 7.88 (d, J = 1.1 Hz, 1H), 7.54 (d, J = 9.3 Hz, 1H), 7.32(dd, J = 9.3, 1.6 Hz, 1H), 5.60-5.58 (m, 1H), 5.04-4.83 (m, 1H), 4.55(s, 1H), 3.95 (q, J = 7.7 Hz, 1H), 3.87 (dd, J = 9.1, 5.8 Hz, 1H),3.79-3.71 (m, 2H), 2.27- 2.13 (m, 2H), 1.91 (s, 1H), 1.67 (dtd, J =23.5, 6.9, 3.7 Hz, 1H), 1.22-1.13 (m, 1H); LCMS (electrospray) m/z 474.1(M + H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-((tetrahydrofuran-3-yl)amino)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 417

¹H NMR (400 MHz, DMSO-d₆) δ 13.67-13.49 (m, 1H), 11.10 (s, 1H), 8.79 (s,1H), 8.52 (d, J = 6.8 Hz, 1H), 8.16 (s, 1H), 7.98 (s, 1H), 7.57 (d, J =9.3 Hz, 1H), 7.35 (dd, J = 1.6, 9.3 Hz, 1H), 5.45 (quin, J = 7.1 Hz,1H), 5.07-4.81 (m, 1H), 2.22- 2.11 (m, 1H), 1.85 (s, 3H), 1.73-1.61 (m,1H), 1.55 (d, J = 7.3 Hz, 3H), 1.17 (tdd, J = 6.3, 9.1, 12.3 Hz, 1H);LCMS (electrospray) m/z 473.2 (M + H)+. H(1S,2S)-N-(6-(7-(1-acetamidoethyl)-5- chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 418

¹H NMR (400 MHz, DMSO-d₆) δ 13.40 (s, 1H), 11.10 (s, 1H), 8.87 (s, 1H),8.16-8.04 (m, 2H), 7.59 (d, J = 8.8 Hz, 1H), 7.41 (dd, J = 9.1, 1.9 Hz,1H), 5.81 (q, J = 7.1 Hz, 1H), 5.04-4.83 (m, 1H), 3.79- 3.58 (m, 2H),2.20-2.13 (m, 1H), 1.67 (dtd, J = 23.4, 6.8, 3.6 Hz, 1H), 1.23 (t, J =7.1 Hz, 3H), 1.19-1.13 (m, 1H); LCMS (electrospray) m/z 514.7 (M + H)+.H (1S,2S)-N-(6-(5-chloro-7-(1-ethoxy-2,2,2-trifluoroethyl)-6-fluoro-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 419

¹H NMR (400 MHz, DMSO-d₆) δ 13.78 (s, 1H), 11.12 (s, 1H), 8.89 (t, J =1.4 Hz, 1H), 8.18 (s, 1H), 8.12 (s, 1H), 7.61 (d, J = 9.3 Hz, 1H), 7.42(dd, J = 9.1, 1.9 Hz, 1H), 7.06 (dt, J = 41.2, 6.7 Hz, 1H), 5.05-4.84(m, 1H), 2.21-2.14 (m, 1H), 1.68 (dtd, J = 23.5, 6.9, 3.5 Hz, 1H),1.24-1.14 (m, 1H); LCMS (electrospray) m/z 488.7 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1,2,2,2-tetrafluoroethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 420

¹H NMR (400 MHz, DMSO-d₆) δ 13.30 (br s, 1H), 11.05 (s, 1H), 8.72 (s,1H), 8.14 (s, 1H), 7.87 (br s, 1H), 7.52 (d, J = 9.2 Hz, 1H), 7.31 (dd,J = 1.5, 9.2 Hz, 1H), 5.34 (br s, 1H), 5.04-4.82 (m, 1H), 2.16 (td, J =7.0, 13.9 Hz, 1H), 1.73-1.61 (m, 1H), 1.26 (d, J = 6.3 Hz, 3H), 1.16(ddd, J = 2.8, 6.2, 12.1 Hz, 1H), 1.00 (br s, 1H), 0.46-0.37 (m, 2H),0.30- 0.20 (m, 2H); LCMS (electrospray) m/z 471.2 (M + H)+. H(1S,2S)-N-(6-(5-chloro-7-((1- cyclopropylethyl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 421

¹H NMR (400 MHz, DMSO-d₆) δ 13.22 (br s, 1H), 11.06 (s, 1H), 8.71 (s,1H), 8.14 (s, 1H), 7.86 (s, 1H), 7.52 (d, J = 9.1 Hz, 1H), 7.30 (d, J =9.3 Hz, 1H), 5.57 (m, 1H), 4.92 (m, 1H), 3.30 (s, 2H), 2.15 (m, 1H),1.66 (m, 1H), 1.16 (m, 1H), 1.07 (m, 1H), 0.48 (m, 2H), 0.27 (m, 2H);LCMS (electrospray) m/z 457.1 (M + H)+. H (1S,2S)-N-(6-(5-chloro-7-((cyclopropylmethyl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 422

¹H NMR (400 MHz, DMSO-d₆) δ 13.52-13.66 (m, 1H), 11.09 (s, 1H), 8.80 (s,1H), 8.16 (s, 1H), 7.97 (s, 1H), 7.57 (d, J = 9.2 Hz, 1H), 7.36 (dd, J =1.6 Hz, 1.6 Hz, 1H), 5.04-4.83 (m, 1H), 3.82- 3.74 (m, 3H), 3.68 (s,1H), 2.20-2.14 (m, 1H), 1.71-1.63 (m, 1H), 1.22 (d, J = 7.4 Hz, 3H),1.2- 1.14(m, 2H); LCMS (electrospray) m/z 460.0 (M + H)+; SFC RT =0.640. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-((R)-1-methoxypropan-2-yl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 423

¹H NMR (400 MHz, DMSO-d₆) δ 13.57 (s, 1H), 11.09 (s, 1H), 8.80 (s, 1H),8.16 (s, 1H), 7.98 (s, 1H), 7.57 (d, J = 9.2 Hz, 1H), 7.35 (d, J = 1.6Hz, 1H), 5.04-4.83 (m, 1H), 3.82-3.74 (m, 3H), 2.20-2.14 (m, 1H),1.41-1.39 (m, 1H), 1.22 (d, J = 14.4 Hz, 3H), 1.2-1.17(m, 2H); LCMS(electrospray) m/z 460.0 (M + H)+; SFC RT = 1.252. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-((S)-1-methoxypropan-2-yl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 424

¹H NMR (400 MHz, DMSO-d₆) δ 13.64-13.32 (m, 1H), 11.09 (s, 1H), 8.79 (s,1H), 8.32 (br d, J = 6.3 Hz, 1H), 8.16 (s, 1H), 7.98 (s, 1H), 7.57 (d, J= 9.3 Hz, 1H), 7.35 (dd, J = 1.7, 9.2 Hz, 1H), 5.46 (br t, J = 7.0 Hz,1H), 5.05-4.81 (m, 1H), 2.19-2.07 (m, 3H), 1.74-1.60 (m, 1H), 1.55 (d, J= 7.3 Hz, 3H), 1.24-1.11 (m, 1H), 0.95 (t, J = 7.6 Hz, 3H); LCMS(electrospray) m/z 487.2 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1- propionamidoethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 425

¹H NMR (400 MHz, DMSO-d₆) δ 13.55-13.09 (m, 1H), 11.07 (s, 1H), 8.73 (s,1H), 8.16 (s, 1H), 8.07- 7.83 (m, 1H), 7.54 (d, J = 9.1 Hz, 1H), 7.32(dd, J = 1.7, 9.1 Hz, 1H), 6.30-5.95 (m, 1H), 5.65-5.44 (m, 1H),5.11-4.76 (m, 1H), 4.54-3.95 (m, 1H), 2.20-2.12 (m, 1H), 1.75-1.59 (m,1H), 1.33 (d, J = 6.7 Hz, 3H), 1.17 (ddt J = 6.2, 6.2, 9.1, 12.2 Hz,1H); LCMS (electrospray) m/z 481.0 (M + H)+. H(1S,2S)-N-(6-(5-chloro-7-((1,1- difluoropropan-2-yl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 426

¹H NMR (400 MHz, DMSO-d₆) δ 13.66-13.47 (m, 1H), 11.09 (s, 1H), 8.80 (s,1H), 8.67 (br d, J = 6.8 Hz, 1H), 8.16 (s, 1H), 8.06 (s, 1H), 8.00 (brs, 1H), 7.57 (d, J = 9.3 Hz, 1H), 7.35 (dd, J = 1.4, 9.3 Hz, 1H),5.62-5.48 (m, 1H), 5.09-4.80 (m, 1H), 2.16 (quin, J = 6.9 Hz, 1H),1.73-1.61 (m, 1H), 1.57 (d, J = 7.0 Hz, 3H), 1.22-1.10 (m, 1H); LCMS(electrospray) m/z 458.9 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1- formamidoethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 427

¹H NMR (400 MHz, DMSO-d₆) δ 13.74-13.07 (m, 1H), 11.09 (s, 1H), 8.80 (s,1H), 8.43 (s, 1H), 8.16 (s, 1H), 7.96 (s, 1H), 7.57 (d, J = 9.2 Hz, 1H),7.35 (dd, J = 1.7, 9.2 Hz, 1H), 5.06-4.80 (m, 1H), 4.60 (t, J = 6.4 Hz,1H), 4.50-4.39 (m, 2H), 4.32 (t, J = 6.5 Hz, 1H), 4.15 (t, J = 6.2 Hz,1H), 3.75 (br t, J = 6.7 Hz, 1H), 2.22-2.11 (m, 1H), 1.73- 1.60 (m, 1H),1.49 (d, J = 6.7 Hz, 3H), 1.24-1.11 (m, 1H); LCMS (electrospray) m/z487.3 (M + H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1-(oxetan-3-ylamino)ethyl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 428

¹H NMR (400 MHz, DMSO-d₆) δ 13.30 (br s, 1H), 11.19 (s, 1H), 10.04 (d, J= 4.5 Hz, 1H), 8.84 (s, 1H), 8.16 (s, 1H), 8.04 (s, 1H), 7.62 (d, J =9.1 Hz, 1H), 7.49-7.39 (m, 1H), 5.70-5.46 (m, 1H), 5.11- 4.78 (m, 1H),2.17 (td, J = 6.9, 13.8 Hz, 1H), 1.69 (d, J = 7.0 Hz, 3H), 1.67-1.59 (m,1H), 1.29-1.09 (m, 1H); LCMS (electrospray) m/z 527.1 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1-(2,2,2-trifluoroacetamido)ethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 429

¹H NMR (400 MHz, DMSO-d₆) δ 13.30 (br s, 1H), 11.05 (s, 1H), 8.72 (s,1H), 8.14 (s, 1H), 7.91 (s, 1H), 7.58 (d, J = 9.0 Hz, 1H), 7.38-7.32 (m,1H), 5.09-4.81 (m, 1H), 4.08-3.99 (m, 1H), 2.19-2.13 (m, 1H), 1.71-1.62(m, 1H), 1.51 (d, J = 6.7 Hz, 3H), 1.32-1.23 (m, 1H), 1.21-1.13 (m, 1H),1.04- 0.94 (m, 1H), 0.69-0.56 (m, 1H); LCMS (electrospray) m/z 496.3(M + H)+. H (1S,2S)-N-(6-(5-chloro-7-(1-((1-cyanocyclopropyl)amino)ethyl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 430

¹H NMR (400 MHz, DMSO-d₆) δ 13.99-13.36 (m, 1H), 11.09 (s, 1H), 8.79 (s,1H), 8.51-8.44 (m, 1H), 8.46 (s, 1H), 8.41 (br d, J = 6.7 Hz, 1H), 8.15(s, 1H), 7.97 (s, 1H), 7.57 (d, J = 9.2 Hz, 1H), 7.35 (dd, J = 1.7, 9.3Hz, 1H), 5.45 (br t, J = 7.0 Hz, 1H), 5.07-4.76 (m, 1H), 3.14-3.03 (m,1H), 2.10 (br d, J = 8.7 Hz, 1H), 2.21-2.01 (m, 1H), 2.00-1.81 (m, 4H),1.64 (dt, J = 4.2, 6.7 Hz, 1H), 1.75-1.60 (m, 1H), 1.55 (br d, J = 7.2Hz, 3H), 1.17 (ddd, J = 2.8, 6.2, 12.3 Hz, 1H); LCMS (electrospray) m/z513.3 (M + H)+. H N-(1-(5-chloro-6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1- carboxamido)imidazo[1,2-a]pyridin-6-yl)-1H-indazol-7- yl)ethyl)cyclobutanecarboxamide 431

¹H NMR (400 MHz, DMSO-d₆) δ 13.37 (br s, 1H), 11.25 (s, 1H), 8.92 (s,1H), 8.81 (d, J = 5.7 Hz, 1H), 8.22 (s, 1H), 8.19 (s, 1H), 8.10 (s, 1H),7.66 (d, J = 9.2 Hz, 1H), 7.49 (d, J = 9.4 Hz, 1H), 5.06-4.89 (m, 1H),2.24-2.15 (m, 1H), 1.78-1.62 (m, 1H), 1.26-1.17 (m, 1H), 0.30-0.20 (m,2H); LCMS (electrospray) m/z 453.9 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1H- imidazol-5-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 432

¹H NMR (400 MHz, DMSO-d₆) δ 13.18 (s, 1H), 11.08 (s, 1H), 8.68 (s, 1H),8.19 (s, 1H), 7.81 (s, 1H), 7.54 (d, J = 9.3 Hz, 1H), 7.30 (dd, J = 9.3,1.6 Hz, 1H), 6.48 (d, J = 18.1 Hz, 2H), 4.93 (ddd, J = 66.4, 10.0, 6.2Hz, 1H), 3.40 (s, 4H), 2.19-2.12 (m, 1H), 1.71-1.62 (m, 1H), 1.19-1.12(m, 1H); LCMS (electrospray) m/z 472.10 (M + H)+. H(1S,2S)-N-(6-(5-chloro-7-((4,5-dihydro-1H-imidazol-2-yl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 433

¹H NMR (400 MHz, DMSO-d₆) δ 1H-NMR (400 MHz, DMSO-D6) δ 13.31 (s, 1H),11.11 (s, 1H), 8.79 (d, J = 1.6 Hz, 1H), 8.19 (s, 1H), 7.98 (d, J = 1.6Hz, 1H), 7.94 (d, J = 4.9 Hz, 1H), 7.58 (d, J = 9.3 Hz, 1H), 7.35 (dd, J= 9.1, 1.9 Hz, 1H), 4.93 (ddd, J = 66.2, 10.2, 6.3 Hz, 1H), 4.25 (q, J =7.1 Hz, 1H), 2.67-2.60 (m, 3H), 2.19-2.08 (m, 1H), 1.71-1.61 (m, 1H),1.55 (d, J = 7.1 Hz, 3H), 1.24- 1.10 (m, 1H); LCMS (electrospray) m/z473.10 (M + H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1-(methylamino)-1-oxopropan-2-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 434

¹H NMR (400 MHz, DMSO-d₆) δ 13.70 (s, 1H), 11.13 (s, 1H), 8.85 (s, 1H),8.18 (s, 1H), 8.04-8.01 (m, 1H), 7.59 (d, J = 9.3 Hz, 1H), 7.39 (dd, J =9.3, 1.6 Hz, 1H), 5.05-4.84 (m, 1H), 4.10 (d, J = 12.6 Hz, 2H),2.20-2.13 (m, 1H), 2.08 (d, J = 9.3 Hz, 3H), 1.67 (dtd, J = 23.3, 6.8,3.7 Hz, 1H), 1.24-1.14 (m, 1H), LCMS (electrospray) m/z 449.05 (M + H)+.H (1S,2S)-N-(6-(5-chloro-6-fluoro-7- ((methylthio)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 435

¹H NMR (400 MHz, DMSO-d₆) δ 13.71 (s, 1H), 11.12 (s, 1H), 8.79 (s, 1H),8.23 (s, 1H), 8.03 (d, J = 1.1 Hz, 1H), 7.60 (d, J = 9.3 Hz, 1H), 7.36(dd, J = 9.3, 1.6 Hz, 1H), 6.42 (s, 1H), 5.04-4.84 (m, 1H), 3.21 (s,3H), 2.58 (d, J = 4.4 Hz, 3H), 2.20-2.13 (m, 1H), 1.70-1.63 (m, 1H),1.19-1.13 (m, 1H) m/z 474.10 (M + H)+. H (1S,2S)-N-(6-(5-chloro-7-(1,3-dimethylureido)-6-fluoro-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 436

¹H NMR (400 MHz, DMSO-d₆) δ 13.58 (s, 1H), 11.12 (s, 1H), 8.82 (t, J =1.4 Hz, 1H), 8.18 (d, J = 12.1 Hz, 1H), 8.01 (s, 1H), 7.58 (d, J = 9.3Hz, 1H), 7.38 (dd, J = 9.3, 1.6 Hz, 1H), 5.04-4.83 (m, 1H), 4.64 (q, J =7.1 Hz, 1H), 2.19-2.12 (m, 1H), 2.02- 1.96 (m, 3H), 1.81-1.77 (m, 3H),1.66 (dtd, J = 23.3, 6.9, 3.8 Hz, 1H), 1.21-1.13 (m, 1H), LCMS(electrospray) m/z 463.00 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1- (methylthio)ethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 437

¹H NMR (400 MHz, DMSO-d₆) δ 13.71 (s, 1H), 11.12 (s, 1H), 8.85 (d, J =1.1 Hz, 1H), 8.21-8.16 (m, 1H), 8.03 (d, J = 1.1 Hz, 1H), 7.59 (d, J =9.3 Hz, 1H), 7.39 (dd, J = 9.3, 1.6 Hz, 1H), 5.04-4.83 (m, 1H),4.54-4.43 (m, 2H), 2.68 (d, J = 13.7 Hz, 3H), 2.20-2.13 (m, 1H), 1.67(dtd, J = 23.3, 6.9, 3.8 Hz, 1H), 1.20-1.13 (m, 1H) LCMS (electrospray)m/z 465.00 (M + H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-((methylsulfinyl)methyl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 438

¹H NMR (400 MHz, DMSO-d₆) δ 13.69 (s, 1H), 11.12 (s, 1H), 8.85 (t, J =1.4 Hz, 1H), 8.18 (s, 1H), 8.04 (s, 1H), 7.59 (d, J = 9.3 Hz, 1H), 7.39(dd, J = 9.3, 1.6 Hz, 1H), 5.04-4.83 (m, 3H), 3.11 (s, 3H), 2.19-2.12(m, 1H), 1.66 (dtd, J = 23.5, 6.7, 3.5 Hz, 1H), 1.22-1.13 (m, 1H), LCMS(electrospray) m/z 481.00 (M + H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-((methylsulfonyl)methyl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 439

¹H NMR (400 MHz, DMSO-d₆) δ 13.81 (s, 1H), 11.14 (s, 1H), 9.65 (d, J =6.0 Hz, 1H), 8.86 (s, 1H), 8.21 (d, J = 8.8 Hz, 2H), 8.13 (s, 1H), 7.61(d, J = 9.3 Hz, 1H), 7.39 (dd, J = 9.1, 1.4 Hz, 1H), 6.69 (d, J = 6.6Hz, 1H), 5.05-4.84 (m, 1H), 2.21-2.14 (m, 1H), 1.73-1.62 (m, 1H),1.22-1.14 (m, 1H), LCMS (electrospray) m/z 471.00 (M + H)+. H(1S,2S)-N-(6-(5-chloro-7- (cyano(formamido)methyl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 440

¹H NMR (400 MHz, DMSO-d₆) δ 13.33 (s, 1H), 11.12 (s, 1H), 8.85 (t, J =1.4 Hz, 1H), 8.16 (s, 1H), 7.97 (d, J = 0.8 Hz, 1H), 7.58 (d, J = 8.8Hz, 1H), 7.39 (dd, J = 9.3, 1.6 Hz, 1H), 5.04-4.83 (m, 2H), 3.93-3.87(m, 1H), 3.38 (d, J = 3.3 Hz, 2H), 3.24 (s, 3H), 2.16 (dt, J = 14.4, 6.7Hz, 1H), 1.66 (dtd, J = 23.2, 6.9, 3.8 Hz, 1H), 1.24-1.13 (m, 1H), 0.95(d, J = 6.0 Hz, 3H); LCMS (electrospray) m/z 490.10 (M + H)+. H(1S,2S)-N-(6-(5-chloro-7-((1S,2R)-1,2-dimethoxypropyl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 441

¹H NMR (400 MHz, DMSO-d₆) δ 13.60 (br s, 1H), 11.08 (s, 1H), 9.39 (br d,J = 6.5 Hz, 1H), 8.80 (s, 1H), 8.16 (s, 1H), 8.02 (br s, 1H), 7.57 (d, J= 9.3 Hz, 1H), 7.36 (dd, J = 1.8, 9.2 Hz, 1H), 6.28 (t, J = 53.6 Hz,1H), 5.55 (br t, J = 6.8 Hz, 1H), 5.04- 4.81 (m, 1H), 2.23-2.10 (m, 1H),1.73-1.67 (m, 1H), 1.65 (d, J = 7.2 Hz, 3H), 1.17 (tdd, J = 6.2, 9.1,12.3 Hz, 1H); LCMS (electrospray) m/z 509.2 (M + H)+. H(1S,2S)-N-(6-(5-chloro-7-(1-(2,2- difluoroacetamido)ethyl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 442

¹H NMR (400 MHz, DMSO-d₆) δ 13.20 (s, 1H), 12.37 (d, J = 1.3 Hz, 1H),11.08 (s, 1H), 8.85 (s, 1H), 8.18 (s, 1H), 8.00 (s, 1H), 7.67 (d, J =3.1 Hz, 1H), 7.58 (d, J = 9.2 Hz, 1H), 7.40 (dd, J = 1.7. 9.2 Hz, 1H),4.93 (m, 1H), 2.48 (s, 3H), 2.16 (m, 2H), 1.67 (m, 2H), 1.17 (m, 2H);LCMS (electrospray) m/z 468.1 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(2-methyl-1H-imidazol-5-yl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 443

¹H NMR (400 MHz, DMSO-d₆) δ 13.68 (s, 1H), 11.11 (s, 1H), 8.81 (d, J =1.1 Hz, 1H), 8.17 (d, J = 9.3 Hz, 1H), 8.05 (d, J = 1.1 Hz, 1H), 7.59(d, J = 9.3 Hz, 1H), 7.37 (dd, J = 9.1, 1.9 Hz, 1H), 5.04- 4.83 (m, 1H),4.64-4.59 (m, 1H), 2.48 (s, 2H), 2.19-2.12 (m, 1H), 1.83-1.81 (m, 3H),1.71-1.61 (m, 1H), 1.20-1.13 (m, 1H); LCMS (electrospray) m/z 478.1 (M +H)+. H (1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1-(methylsulflnyl)ethyl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 444

¹H NMR (400 MHz, DMSO-d₆) δ 13.54 (s, 1H), 11.12 (s, 1H), 8.84 (s, 1H),8.18 (s, 1H), 8.04 (s, 1H), 7.60 (d, J = 9.3 Hz, 1H), 7.38 (dd, J = 9.3,1.6 Hz, 1H), 5.15 (d, J = 7.1 Hz, 1H), 5.04-4.83 (m, 1H), 3.06 (s, 3H),2.20-2.13 (m, 1H), 1.97-1.91 (m, 3H), 1.72-1.62 (m, 1H), 1.20-1.13 (m,1H); LCMS (electrospray) m/z 494.1 (M + H)+. H(1S,2S)-N-(6-(5-chloro-6-fluoro-7-(1-(methylsulfonyl)ethyl)-1H-indazol-4- yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 445

¹H NMR (400 MHz, DMSO-d₆) δ 13.26 (s, 1H), 11.08 (s, 1H), 8.79 (s, 1H),8.18 (s, 1H), 8.00 (d, J = 23.6 Hz, 2H), 7.58 (d, J = 8.8 Hz, 1H), 7.35(dd, J = 9.1, 1.9 Hz, 1H), 5.04-4.83 (m, 1H), 4.24 (q, J = 7.1 Hz, 1H),3.11 (td, J = 12.6, 7.1 Hz, 2H), 2.20- 2.13 (m, 1H), 1.70-1.63 (m, 1H),1.54 (d, J = 7.1 Hz, 3H), 1.21-1.13 (m, 1H), 1.01 (t, J = 7.1 Hz, 3H);LCMS (electrospray) m/z 487.1 (M + H)+. H(1S,2S)-N-(6-(5-chloro-7-(1-(ethylamino)-1-oxopropan-2-yl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 446

¹H NMR (400 MHz, DMSO-d₆) δ 13.09 (s, 1H), 11.13 (s, 1H), 8.61 (d, J =7.1 Hz, 1H), 7.74 (s, 1H), 7.63 (d, J = 0.9 Hz, 1H), 7.49 (d, J = 8.6Hz, 1H), 7.32 (d, J = 8.6 Hz, 1H), 6.91 (s, 1H), 6.86 (dd, J = 1.9, 7.0Hz, 1H), 5.06-4.98 (m, 1H), 4.88-4.84 (m, 1H), 2.34 (s, 3H), 2.15 (td, J= 6.9, 13.8 Hz, 1H), 1.74- 1.61 (m, 1H), 1.21-1.13 (m, 1H); LCMS(electrospray) m/z 350.1 (M + H)+. J (1S,2S)-2-fluoro-N-(5-(5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide 447

¹H NMR (400 MHz, DMSO-d₆) δ 11.16 (s, 1H), 8.63 (d, J = 7.1 Hz, 1H),7.82 (s, 1H), 7.65 (d, J = 0.9 Hz, 1H), 7.45 (d, J = 11.5 Hz, 1H), 6.93(s, 1H), 6.81 (dd, J = 1.8, 7.1 Hz, 1H), 6.56 (dd, J = 11.8, 17.9 Hz,1H), 5.63 (br d, J = 18.0 Hz, 1H), 5.46-5.36 (m, 1H), 5.06-4.82 (m, 1H),2.15 (td, J = 7.0, 13.8 Hz, 1H), 1.73-1.59 (m, 1H), 1.17 (tdd, J = 6.3,9.0, 12.3 Hz, 1H)); LCMS (electrospray) m/z 380.1 (M + H)+. J(1S,2S)-2-fluoro-N-(5-(6-fluoro-5-vinyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide.2 HCl 448

¹H NMR (400 MHz, DMSO-d₆) δ 11.16 (s, 1H), 8.65 (d, J = 7.1 Hz, 1H),7.88 (d, J = 1.0 Hz, 1H), 7.75 (d, J = 1.0 Hz, 1H), 7.63 (dd, J = 1.0,8.8 Hz, 1H), 7.51 (d, J = 8.8 Hz, 1H), 6.95 (s, 1H), 6.92 (dd, J = 2.0,7.1 Hz, 1H), 5.05-4.83 (m, 1H), 2.15 (td, J = 7.0, 13.8 Hz, 1H),1.74-1.60 (m, 1H), 1.17 (tdd, J = 6.3, 9.0, 12.3 Hz, 1H); LCMS(electrospray) m/z 370.1 (M + H)+. J(1S,2S)-N-(5-(5-chloro-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 HCl 449

¹H NMR (400 MHz, DMSO-d₆) δ 11.10 (s, 1H), 8.56 (br d, J = 7.0 Hz, 1H),7.90 (s, 1H), 7.74 (s, 1H), 7.58 (br d, J = 9.2 Hz, 1H), 7.35 (d, J =8.9 Hz, 1H), 6.98 (br d, J = 7.1 Hz, 1H), 6.89 (s, 1H), 5.08- 4.80 (m,1H), 3.80 (s, 3H), 2.19-2.08 (m, 1H), 1.75-1.60 (m, 1H), 1.26-1.07 (m,1H); LCMS (electrospray) m/z 366.1 (M + H)+. J(1S,2S)-2-fluoro-N-(5-(5-methoxy-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide. 2HCl 450

¹H NMR (400 MHz, DMSO-d₆) δ 11.18 (br s, 1H), 8.68 (br s, 1H), 8.12-7.54(m, 5H), 7.04-6.85 (m, 2H), 5.05-4.84 (m, 1H), 3.10 (br s, 6H), 2.16(td, J = 7.0, 14.0 Hz, 1H), 1.73-1.62 (m, 1H), 1.23-1.14 (m, 1H); LCMS(electrospray) m/z 379.1 (M + H)+. J (1S,2S)-N-(5-(5-(dimethylamino)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 3 HCl 451

¹H NMR (400 MHz, DMSO-d₆) δ 14.19-13.15 (m, 1H), 11.17 (s, 1H), 8.64 (d,J = 7.1 Hz, 1H), 7.87 (s, 1H), 7.82-7.74 (m, 2H), 7.64 (s, 1H), 6.93 (s,1H), 6.83 (dd, J = 1.8, 7.1 Hz, 1H), 5.08-4.81 (m, 1H), 2.20-2.10 (m,1H), 1.74-1.59 (m, 1H), 1.17 (tdd, J = 6.2, 9.0, 12.4 Hz, 1H); LCMS(electrospray) m/z 404.1 (M + H)+. J (1S,2S)-2-fluoro-N-(5-(5-(trifluoromethyl)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropane-1-carboxamide. 2 HCl 452

¹H NMR (400 MHz, DMSO-d₆) δ 13.10 (br s, 1H), 11.13 (s, 1H), 8.61 (d, J= 7.1 Hz, 1H), 7.68 (s, 1H), 7.59 (d, J = 1.0 Hz, 1H), 7.53 (d, J = 8.6Hz, 1H), 7.36 (d, J = 8.7 Hz, 1H), 6.90 (s, 1H), 6.81 (dd, J = 1.9, 7.0Hz, 1H), 5.06-4.81 (m, 1H), 2.70-2.59 (m, 2H), 2.20-2.10 (m, 1H),1.75-1.58 (m, 1H), 1.18 (td, J = 3.1, 6.1 Hz, 1H), 1.12 (t, J = 7.5 Hz,3H); LCMS (electrospray) m/z 364.2 (M + H)+. J(1S,2S)-N-(5-(5-ethyl-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 453

¹H NMR (400 MHz, DMSO-d₆) δ 11.16 (s, 1H), 8.61 (d, J = 7.1 Hz, 1H),7.97 (d, J = 0.7 Hz, 1H), 7.77 (d, J = 8.8 Hz, 1H), 7.69-7.64 (m, 1H),7.61 (d, J = 1.1 Hz, 1H), 6.92 (s, 1H), 6.82 (dd, J = 2.0, 7.1 Hz, 1H),5.06-4.82 (m, 1H), 2.33 (s, 3H), 2.21- 2.11 (m, 1H), 1.73-1.61 (m, 1H),1.18 (tdd, J = 6.1, 8.9, 12.3 Hz, 1H); LCMS (electrospray) m/z 378.2(M + H)+. J (1S,2S)-N-(5-(5-acetyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 2HCl 454

¹H NMR (400 MHz, DMSO-d₆) δ 11.11 (s, 1H), 8.58 (d, J = 7.1 Hz, 1H),7.82 (s, 1H), 7.66 (s, 1H), 7.40 (d, J = 12.0 Hz, 1H), 6.93-6.87 (m,2H), 5.05- 4.82 (m, 1H), 2.67 (s, 6H), 2.19-2.09 (m, 1H), 1.73-1.61 (m,1H), 1.22-1.12 (m, 1H); LCMS (electrospray) m/z = 397.1 (M + H+) J(1S,2S)-N-(5-(5-(dimethylamino)-6- fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 3 TFA 455

¹H NMR (400 MHz, DMSO-d₆) δ 13.43 (br s, 1H), 11.15 (s, 1H), 8.65 (d, J= 7.1 Hz, 1H), 7.83 (s, 1H), 7.70 (dd, J = 0.8, 1.8 Hz, 1H), 7.67-7.63(m, 1H), 7.58-7.55 (m, 1H), 6.95 (s, 1H), 6.88 (dd, J = 1.9, 7.2 Hz,1H), 5.05-4.83 (m, 1H), 2.20-2.10 (m, 1H), 1.72-1.61 (m, 1H), 1.18 (qd,J = 6.2, 15.1 Hz, 1H); LCMS (electrospray) m/z = 414.0 (M + H+) J(1S,2S)-N-(5-(5-bromo-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 456

¹H NMR (400 MHz, DMSO-d₆) δ 11.21 (s, 1H), 8.73 (d, J = 7.2 Hz, 1H),8.19 (s, 1H), 7.94 (d, J = 1.2 Hz, 1H), 7.85-7.73 (m, 2H), 7.09 (dd, J =2.0, 7.1 Hz, 1H), 7.02 (s, 1H), 5.08-4.82 (m, 1H), 2.16 (td, J = 7.0,13.8 Hz, 1H), 1.74-1.62 (m, 1H), 1.18 (tdd, J = 6.3, 9.1, 12.3 Hz, 1H);LCMS (electrospray): m/z = 361.1 (M + H+) J(1S,2S)-N-(5-(5-cyano-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 HCl 457

¹H NMR (400 MHz, DMSO-d₆) δ 11.14 (s, 1H), 8.62 (d, J = 7.1 Hz, 1H),7.83 (s, 1H), 7.74 (d, J = 0.9 Hz, 1H), 7.34 (d, J = 10.5 Hz, 1H), 6.98(dd, J = 1.8, 7.1 Hz, 1H), 6.92 (s, 1H), 5.06-4.99 (m, 1H), 4.90- 4.82(m, 1H), 2.15 (td, J = 7.0, 13.6 Hz, 1H), 2.01- 1.93 (m, 1H), 1.74-1.61(m, 1H), 1.22-1.13 (m, 1H), 0.77-0.69 (m, 2H), 0.33-0.25 (m, 2H); LCMS(electrospray) m/z = 394.1 (M + H+) J(1S,2S)-N-(5-(5-cyclopropyl-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 458

¹H NMR (400 MHz, DMSO-d₆) δ 13.50 (br s, 1H), 11.17 (s, 1H), 8.68 (d, J= 7.2 Hz, 1H), 7.92 (s, 1H), 7.79 (d, J = 1.0 Hz, 1H), 7.68 (dd, J =0.9, 9.0 Hz, 1H), 6.97 (s, 1H), 6.96 (d, J = 2.0 Hz, 1H), 6.96- 6.93 (m,1H), 5.06-5.00 (m, 1H), 4.88-4.84 (m, 1H), 2.18-2.12 (m, 1H), 1.75-1.59(m, 1H), 1.22- 1.14 (tdd, J = 6.2, 9.2, 12.4 Hz, 1H); LCMS(electrospray)m/z = 388.0 (M + H+) J (1S,2S)-N-(5-(5-chloro-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 459

¹H NMR (400 MHz, DMSO-d₆) δ 13.10 (s, 1H), 11.15 (s, 1H), 8.62 (d, J =7.1 Hz, 1H), 7.75-7.67 (m, 2H), 7.48 (d, J = 8.8 Hz, 1H), 7.02 (d, J =8.8 Hz, 1H), 6.96-6.88 (m, 2H), 5.07-4.82 (m, 1H), 2.20- 2.08 (m, 1H),2.03-1.94 (m, 1H), 1.74-1.60 (m, 1H), 1.22-1.11 (m, 1H), 0.90-0.78 (m,2H), 0.70- 0.60 (m, 2H); LCMS (electrospray) m/z = 376.1 (M + H+) J(1S,2S)-N-(5-(5-cyclopropyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 2TFA 460

¹H NMR (400 MHz, DMSO-d₆) δ 13.17 (br s, 1H), 11.15 (s, 1H), 8.64 (d, J= 7.1 Hz, 1H), 7.77 (s, 1H), 7.67 (d, J = 0.9 Hz, 1H), 7.38 (d, J = 9.9Hz, 1H), 6.93 (s, 1H), 6.87 (dd, J = 2.0, 7.1 Hz, 1H), 5.06-4.81 (m,1H), 2.23 (d, J = 2.6 Hz, 3H), 2.15 (td, J = 6.9, 13.8 Hz, 1H),1.75-1.59 (m, 1H), 1.17 (tdd, J = 6.3, 9.1, 12.3 Hz, 1H); LCMS(electrospray) m/z = 368.1 (M + H+) J(1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide.2 TFA 461

¹H NMR (400 MHz, DMSO-d₆) δ 13.18 (br s, 1H), 11.14 (s, 1H), 8.62 (d, J= 7.1 Hz, 1H), 7.82 (s, 1H), 7.69 (s, 1H), 7.58 (s, 2H), 6.94 (dd, J =1.9, 7.0 Hz, 1H), 6.91 (s, 1H), 5.09-4.80 (m, 1H), 4.50 (s, 2H),2.22-2.09 (m, 1H), 1.75-1.58 (m, 1H), 1.24-1.11 (m, 1H); LCMS(electrospray) m/z = 366.0 (M + H+) J (1S,2S)-2-fluoro-N-(5-(5-(hydroxymethyl)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropane-1-carboxamide. 2 TFA 462

¹H NMR (400 MHz, DMSO-d₆) δ 11.14 (s, 1H), 8.63 (d, J = 7.0 Hz, 1H),7.64 (d, J = 3.1 Hz, 1H), 7.59 (d, J = 0.8 Hz, 1H), 7.36 (d, J = 12.3Hz, 1H), 6.92 (s, 1H), 6.78 (dd, J = 1.8, 7.1 Hz, 1H), 5.07-4.97 (m,1H), 4.88-4.84 (m, 1H), 3.13-3.00 (m, 1H), 2.18- 2.11 (m, 1H), 1.74-1.60(m, 1H), 1.28 (dd, J = 7.1, 11.6 Hz, 6H), 1.21-1.08 (m, 1H); LCMS(electrospray) m/z = 396.1 (M + H+) J (1S,2S)-2-fluoro-N-(5-(6-fluoro-5-isopropyl-1H-indazol-4-yl)pyrazolo[1,5- a]pyridin-2-yl)cyclopropane-1-carboxamide. 2 TFA 463

¹H NMR (400 MHz, DMSO-d₆) δ 13.25 (br s, 1H), 11.33-10.98 (m, 1H), 11.13(s, 1H), 8.61 (d, J = 7.0 Hz, 1H), 7.76 (s, 1H), 7.66-7.59 (m, 2H),7.56-7.51 (m, 1H), 6.92 (s, 1H), 6.87 (dd, J = 1.8, 7.1 Hz, 1H),5.23-4.71 (m, 1H), 2.39 (s, 3H), 2.20-2.10 (m, 1H), 1.75-1.58 (m, 1H),1.17 (tdd, J = 6.2, 9.1, 12.2 Hz, 1H); LCMS (electrospray) m/z = 382.1(M + H+) J (1S,2S)-2-fluoro-N-(5-(5-(methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide. 2TFA 464

¹H NMR (400 MHz, DMSO-d₆) δ 13.48 (br s, 1H), 11.17 (s, 1H), 8.67 (d, J= 7.1 Hz, 1H), 7.86 (s, 1H), 7.74 (d, J = 1.0 Hz, 1H), 7.66-7.61 (m,1H), 6.96 (s, 1H), 6.90 (dd, J = 2.0, 7.1 Hz, 1H), 5.08-4.80 (m, 1H),2.14 (br d, J = 7.2 Hz, 1H), 1.75-1.60 (m, 1H), 1.21-1.14 (m, 1H); LCMS(electrospray) m/z = 432.0 (M + H+) J (1S,2S)-N-(5-(5-bromo-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 465

¹H NMR (400 MHz, DMSO-d₆) δ 13.52 (br s, 1H), 11.17 (s, 1H), 8.67 (d, J= 7.0 Hz, 1H), 7.94 (s, 1H), 7.78-7.74 (m, 1H), 7.73-7.69 (m, 1H), 7.66(s, 1H), 7.11-6.80 (m, 3H), 5.07-4.83 (m, 1H), 2.19- 2.10 (m, 1H),1.74-1.62 (m, 1H), 1.18 (tdd, J = 6.4, 9.0, 12.3 Hz, 1H); LCMS(electrospray) m/z = 386.2 (M + H+) J(1S,2S)-N-(5-(5-(difluoromethyl)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 466

¹H NMR (400 MHz, DMSO-d₆) δ 11.15 (s, 1H), 8.64 (d, J = 7.1 Hz, 1H),7.70 (s, 1H), 7.63 (s, 1H), 7.39 (d, J = 10.4 Hz, 1H), 6.93 (s, 1H),6.82 (dd, J = 1.8, 7.0 Hz, 1H), 5.06-4.81 (m, 1H), 2.66-2.57 (m, 2H),2.20-2.09 (m, 1H), 1.74-1.60 (m, 1H), 1.22-1.14 (m, 1H), 1.10 (t, J =7.4 Hz, 3H); LCMS (electrospray) m/z = 382.1 (M + H+) J(1S,2S)-N-(5-(5-ethyl-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 467

¹H NMR (400 MHz, DMSO-d₆) δ 13.27 (s, 1H), 11.15 (s, 1H), 8.67-8.61 (m,1H), 7.97 (s, 1H), 7.84-7.80 (m, 1H), 7.56-7.48 (m, 1H), 7.05-6.99 (m,1H), 6.95 (s, 1H), 5.08-4.82 (m, 1H), 3.67 (s, 2H), 3.71-3.63 (m, 1H),2.07 (s, 1H), 1.75-1.61 (m, 1H), 1.26-1.09 (m, 1H); LCMS (electrospray)m/z = 384.1 (M + H+) J (1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methoxy-1H-indazol-4-yl)pyrazolo[1,5- a]pyridin-2-yl)cyclopropane-1-carboxamide. 2 TFA 468

¹H NMR (400 MHz, DMSO-d₆) δ 13.60 (br s, 1H), 11.21 (s, 1H), 8.68 (d, J= 7.1 Hz, 1H), 7.93 (s, 1H), 7.69 (s, 1H), 7.60 (d, J = 11.2 Hz, 1H),7.09-6.79 (m, 3H), 5.08-4.81 (m, 1H), 2.19-2.11 (m, 1H), 1.73-1.61 (m,1H), 1.23-1.14 (m, 1H); LCMS (electrospray) m/z = 404.1 (M + H+) J(1S,2S)-N-(5-(5-(difluoromethyl)-6- fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA 469

¹H NMR (400 MHz, DMSO-d₆) δ 13.40 (s, 1H), 11.14 (br d, J = 3.1 Hz, 1H),8.62 (d, J = 7.0 Hz, 1H), 7.52 (s, 1H), 7.44 (d, J = 9.8 Hz, 1H), 6.90(s, 1H), 6.74 (dd, J = 1.8, 7.1 Hz, 1H), 5.09-4.79 (m, 1H), 2.19-2.12(m, 1H), 2.09 (t, J = 2.4 Hz, 3H), 1.75- 1.60 (m, 1H), 1.23-1.09 (m,1H); LCMS (electrospray) m/z = 402.0 (M + H+) J(1S,2S)-N-(5-(3-chloro-6-fluoro-5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 470

¹H NMR (400 MHz, DMSO-d₆) δ 11.16 (d, J = 3.5 Hz, 1H), 8.63 (d, J = 7.0Hz, 1H), 7.53 (d, J = 0.7 Hz, 1H), 7.29 (d, J = 10.0 Hz, 1H), 6.91 (s,1H), 6.75 (dd, J = 1.8, 7.0 Hz, 1H), 5.11-4.79 (m, 1H), 2.15 (td, J =6.8, 13.4 Hz, 1H), 2.07 (t, J = 2.4 Hz, 3H), 1.90 (d, J = 4.3 Hz, 3H),1.74-1.59 (m, 1H), 1.24- 1.10 (m, 1H); LCMS (electrospray) m/z 382.0(M + H)+. J (1S,2S)-2-fluoro-N-(5-(6-fluoro-3,5-dimethyl-1H-indazol-4-yl)pyrazolo[1,5- a]pyridin-2-yl)cyclopropane-1-carboxamide. 2 TFA s 471

¹H NMR (400 MHz, DMSO-d₆) δ 13.37 (s, 1H), 11.15 (s, 1H), 8.59 (d, J =7.1 Hz, 1H), 7.60 (d, J = 1.0 Hz, 1H), 6.95 (d, J = 10.1 Hz, 1H), 6.91(s, 1H), 6.88 (dd, J = 2.0, 7.1 Hz, 1H), 5.11-4.77 (m, 1H), 2.43 (s,6H), 2.14 (td, J = 6.9, 13.9 Hz, 1H), 1.74-1.60 (m, 1H), 1.24-1.11 (m,1H); LCMS (electrospray) m/z 414.4 (M + H)+. J(1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl- 3-(methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide. 2 TFA 472

¹H NMR (400 MHz, DMSO-d₆) δ 13.53 (s, 1H), 11.15 (br d, J = 5.6 Hz, 1H),8.59 (d, J = 7.0 Hz, 1H), 7.52 (s, 1H), 7.45 (d, J = 9.7 Hz, 1H), 6.90(s, 1H), 6.75 (dd, J = 1.7, 7.0 Hz, 1H), 5.09-4.80 (m, 1H), 3.79 (d, J =2.9 Hz, 1H), 2.20-2.14 (m, 1H), 2.12 (br d, J = 1.7 Hz, 3H), 1.74-1.59(m, 1H), 1.27- 1.08 (m, 1H); LCMS (electrospray) m/z 392.2 (M + H+) J(1S,2S)-N-(5-(3-ethynyl-6-fluoro-5- methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 473

¹H NMR (400 MHz, METHANOL-d₄) δ 8.49 (d, J = 7.2 Hz, 1H), 7.51 (s, 1H),7.17 (d, J = 9.7 Hz, 1H), 6.80 (br d, J = 5.4 Hz, 1H), 4.98-4.76 (m,1H), 2.15 (s, 3H), 2.12-2.03 (m, 1H), 1.87-1.73 (m, 1H), 1.40-1.30 (m,1H), 1.27-1.15 (m, 1H), 0.83-0.74 (m, 1H), 0.69 (br s, 1H), 0.55-0.40(m, 2H); LCMS (electrospray) m/z 408.4 (M + H+) J(1S,2S)-N-(5-(3-cyclopropyl-6-fluoro-5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA 474

¹H NMR (400 MHz, DMSO-d₆) δ 11.17 (d, J = 4.4 Hz, 1H), 8.67 (d, J = 7.1Hz, 1H), 7.53 (s, 1H), 7.37 (d, J = 9.8 Hz, 1H), 6.91 (s, 1H), 6.73 (dd,J = 1.8, 7.1 Hz, 1H), 6.04-5.92 (m, 1H), 5.85-5.75 (m, 1H), 5.06-4.82(m, 2H), 2.15 (br d, J = 6.5 Hz, 1H), 2.07 (t, J = 2.4 Hz, 3H),1.74-1.60 (m, 1H), 1.24-1.11 (m, 1H); LCMS (electrospray) m/z 394.3 (M +H+) J (1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl-3-vinyl-1H-indazol-4-yl)pyrazolo[1,5- a]pyridin-2-yl)cyclopropane-1-carboxamide. 2 TFA 475

¹H NMR (400 MHz, DMSO-d₆) δ 11.16 (br d, J = 4.8 Hz, 1H), 8.63 (d, J =7.1 Hz, 1H), 7.55 (s, 1H), 7.29 (d, J = 9.9 Hz, 1H), 6.90 (s, 1H), 6.76(dd, J = 1.8, 7.0 Hz, 1H), 5.07-4.81 (m, 1H), 2.31-2.24 (m, 2H), 2.14(br d, J = 6.7 Hz, 1H), 2.06 (t, J = 2.4 Hz, 3H), 1.75-1.59 (m, 1H),1.24-1.09 (m, 1H), 0.90 (dt, J = 4.0, 7.5 Hz, 3H); LCMS (electrospray)m/z 396.3 (M + H+) J (1S,2S)-N-(5-(3-ethyl-6-fluoro-5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 476

¹H NMR (400 MHz, DMSO-d₆) δ 14.12 (br d, J = 0.7 Hz, 1H), 11.18 (s, 1H),8.69 (d, J = 7.2 Hz, 1H), 8.04 (br s, 1H), 7.80 (s, 1H), 6.98 (s, 1H),6.95 (dd, J = 1.8, 7.1 Hz, 1H), 5.05-4.84 (m, 1H), 2.18- 2.11 (m, 1H),1.73-1.62 (m, 1H), 1.23-1.15 (m, 1H); LCMS (electrospray) m/z 422.1 (M +H)+. J (1S,2S)-N-(5-(5,7-dichloro-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 477

¹H NMR (400 MHz, DMSO-d₆) δ 13.31 (br s, 1H), 11.14 (s, 1H), 8.63 (d, J= 7.1 Hz, 1H), 7.77 (s, 1H), 7.63 (d, J = 1.0 Hz, 1H), 6.92 (s, 1H),6.84 (dd, J = 1.8, 7.1 Hz, 1H), 5.11-4.75 (m, 1H), 2.47 (d, J = 1.6 Hz,3H), 2.22 (d, J = 2.9 Hz, 3H), 2.15 (td, J = 6.8, 13.8 Hz, 1H),1.74-1.60 (m, 1H), 1.17 (tdd, J = 6.3, 9.1, 12.4 Hz, 1H); LCMS(electrospray) m/z 382.4 (M + H)+. J(1S,2S)-2-fluoro-N-(5-(6-fluoro-5,7-dimethyl-1H-indazol-4-yl)pyrazolo[1,5- a]pyridin-2-yl)cyclopropane-1-carboxamide. 2 TFA 478

¹H NMR (400 MHz, DMSO-d₆) δ 13.16-12.54 (m, 1H), 11.20 (s, 1H), 8.71 (d,J = 7.2 Hz, 1H), 8.00 (s, 1H), 7.82 (s, 1H), 7.00 (s, 1H), 6.96 (dd, J =1.8, 7.2 Hz, 1H), 5.11-4.79 (m, 1H), 2.15 (td, J = 6.9, 13.8 Hz, 1H),1.96 (s, 3H), 1.92 (s, 3H), 1.76-1.60 (m, 1H), 1.18 (tdd, J = 6.4, 9.1,12.2 Hz, 1H); LCMS (electrospray) m/z 464.1 (M + H)+. J(1S,2S)-N-(5-(5-chloro-7- (dimethylphosphoryl)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 479

¹H NMR (400 MHz, DMSO-d₆) δ 13.80 (br s, 1H), 11.17 (s, 1H), 8.66 (d, J= 7.1 Hz, 1H), 7.90 (br s, 1H), 7.69 (s, 1H), 6.94 (s, 1H), 6.87 (dd, J= 2.0, 7.1 Hz, 1H), 5.10-4.78 (m, 1H), 2.27 (d, J = 2.8 Hz, 3H),2.19-2.07 (m, 1H), 1.74-1.60 (m, 1H), 1.24- 1.11 (m, 1H); LCMS(electrospray) m/z 402.0 (M + H)+. J(1S,2S)-N-(5-(7-chloro-6-fluoro-5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 480

¹H NMR (400 MHz, DMSO-d₆) δ 14.00 (br s, 1H), 11.18 (s, 1H), 8.68 (d, J= 7.2 Hz, 1H), 8.08 (br s, 1H), 7.80 (d, J = 0.8 Hz, 1H), 6.98 (s, 1H),6.95 (dd, J = 1.9, 7.2 Hz, 1H), 5.08-4.79 (m, 1H), 2.15 (td, J = 7.0,13.6 Hz, 1H), 1.75-1.60 (m, 1H), 1.26- 1.09 (m, 1H); LCMS (electrospray)m/z 466.3 (M + H)+. J (1S,2S)-N-(5-(7-bromo-5-chloro-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 481

¹H NMR (400 MHz, METHANOL-d₄) δ 8.54 (d, J = 7.1 Hz, 1H), 7.85 (d, J =3.2 Hz, 1H), 7.59 (s, 1H), 6.98 (s, 1H), 6.86 (dd, J = 1.9, 7.2 Hz, 1H),5.00- 4.96 (m, 1H), 2.34 (d, J = 3.2 Hz, 3H), 2.20-2.16 (m, 1H),1.92-1.72 (m, 1H), 1.30-1.15 (m, 1H); LCMS (electrospray) m/z 386.0 (M +H)+. J (1S,2S)-N-(5-(6,7-difluoro-5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 482

¹H NMR (400 MHz, METHANOL-d₄) δ 8.55 (d, J = 7.1 Hz, 1H), 7.89 (s, 1H),7.63 (s, 1H), 7.00 (s, 1H), 6.87 (dd, J = 1.7, 7.1 Hz, 1H), 4.99-4.91(m, 1H), 2.31 (d, J = 3.1 Hz, 3H), 2.14-2.04 (m, 1H), 1.87-1.75 (m, 1H),1.27-1.16 (m, 1H); LCMS (electrospray) m/z 435.9 (M + H)+. J(1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl-7-(trifluoromethyl)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropane-1-carboxamide. 2 TFA 483

¹H NMR (400 MHz, DMSO-d₆) δ 13.36 (br s, 1H), 11.16 (s, 1H), 8.63 (d, J= 7.1 Hz, 1H), 7.81 (s, 1H), 7.65 (s, 1H), 7.52 (s, 1H), 7.15 (dd, J =11.1, 18.0 Hz, 1H), 6.92 (s, 1H), 6.87 (dd, J = 1.8, 7.1 Hz, 1H), 6.11(br d, J = 17.6 Hz, 1H), 5.51 (d, J = 11.6 Hz, 1H), 5.05-4.85 (m, 1H),2.36 (s, 3H), 2.14 (br d, J = 8.1 Hz, 1H), 1.72-1.64 (m, 1H), 1.21-1.15(m, 1H); LCMS (electrospray) m/z 376.1 (M + H)+. J(1S,2S)-2-fluoro-N-(5-(5-methyl-7-vinyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide.2 TFA 484

¹H NMR (400 MHz, DMSO-d₆) δ 13.51 (br s, 1H), 11.16 (s, 1H), 8.64 (d, J= 7.1 Hz, 1H), 7.87 (s, 1H), 7.73 (d, J = 1.0 Hz, 1H), 6.95 (s, 1H),6.91 (dd, J = 1.9, 7.2 Hz, 1H), 5.10-4.78 (m, 1H), 3.00 (br s, 6H), 2.15(td, J = 7.0, 13.8 Hz, 1H), 1.74-1.61 (m, 1H), 1.24-1.11 (m, 1H); LCMS(electrospray) m/z 431.1 (M + H)+. J (1S,2S)-N-(5-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 2TFA 485

¹H NMR (400 MHz, DMSO-d₆) δ 13.79 (s, 1H), 11.17 (s, 1H), 8.68 (d, J =7.1 Hz, 1H), 7.98 (s, 1H), 7.79 (d, J = 1.0 Hz, 1H), 6.98 (s, 1H), 6.94(dd, J = 2.0, 7.1 Hz, 1H), 5.08-4.77 (m, 1H), 2.57 (s, 3H), 2.15 (td, J= 6.9, 13.9 Hz, 1H), 1.74-1.61 (m, 1H), 1.18 (tdd, J = 6.3, 9.1, 12.3Hz, 1H); LCMS (electrospray) m/z 434.2 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7- (methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 2TFA 486

¹H NMR (400 MHz, DMSO-d₆) δ 13.51 (br s, 1H), 11.20 (s, 1H), 8.72 (d, J= 7.2 Hz, 1H), 8.10 (s, 1H), 7.84 (d, J = 1.0 Hz, 1H), 7.02 (s, 1H),6.96 (dd, J = 1.9, 7.2 Hz, 1H), 5.07-4.77 (m, 1H), 3.56 (s, 3H), 2.15(quin, J = 6.9 Hz, 1H), 1.75-1.58 (m, 1H), 1.18 (tdd, J = 6.3, 9.0, 12.3Hz, 1H); LCMS (electrospray) m/z 466.1 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7- (methylsulfonyl)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 2TFA 487

¹H NMR (400 MHz, DMSO-d₆) δ 13.69 (br s, 1H), 11.19 (s, 1H), 8.66 (d, J= 7.0 Hz, 1H), 7.92 (br s, 1H), 7.69 (d, J = 1.0 Hz, 1H), 6.94 (s, 1H),6.87 (dd, J = 1.9, 7.1 Hz, 1H), 5.07-4.82 (m, 1H), 2.27 (d, J = 3.0 Hz,3H), 2.20-2.10 (m, 1H), 1.74-1.60 (m, 1H), 1.18 (tdd, J = 6.2, 9.1, 12.3Hz, 1H); LCMS (electrospray) m/z 448.1 (M + H)+. J(1S,2S)-N-(5-(7-bromo-6-fluoro-5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 488

¹H NMR (400 MHz, DMSO-d₆) δ 13.49 (s, 1H), 11.18 (s, 1H), 8.65 (d, J =7.0 Hz, 1H), 7.84 (s, 1H), 7.68 (s, 1H), 6.93 (s, 1H), 6.87 (dd, J =1.9, 7.1 Hz, 1H), 5.05-4.84 (m, 1H), 2.52 (br s, 3H), 2.24 (d, J = 2.9Hz, 3H), 2.19-2.10 (m, 1H), 1.73-1.61 (m, 1H), 1.22-1.13 (m, 1H); LCMS(electrospray) m/z 414.2 (M + H)+. J(1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl- 7-(methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide. 2 TFA 489

¹H NMR (400 MHz, DMSO-d₆) δ 13.23 (s, 1H), 11.21 (s, 1H), 8.70 (d, J =7.2 Hz, 1H), 7.95 (s, 1H), 7.74 (d, J = 0.9 Hz, 1H), 6.97 (s, 1H), 6.90(dd, J = 1.9, 7.2 Hz, 1H), 5.05-4.84 (m, 1H), 3.50 (s, 3H), 2.27 (d, J =2.8 Hz, 3H), 2.15 (td, J = 6.9, 13.9 Hz, 1H), 1.73-1.62 (m, 1H),1.25-1.12 (m, 1H); LCMS (electrospray) m/z 446.2 (M + H)+. J(1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl-7-(methylsulfonyl)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropane-1-carboxamide. 2 TFA 490

¹H NMR (400 MHz, DMSO-d₆) δ 11.14 (s, 1H), 8.62 (d, J = 7.2 Hz, 1H),7.75 (s, 1H), 7.61 (d, J = 1.0 Hz, 1H), 6.90 (s, 1H), 6.84 (dd, J = 1.9,7.1 Hz, 1H), 5.05-5.00 (m, 1H), 4.88-4.83 (m, 1H), 2.96 (d, J = 2.0 Hz,6H), 2.20 (d, J = 3.4 Hz, 3H), 2.17- 2.09 (m, 1H), 1.73-1.61 (m, 1H),1.21-1.12 (m, 1H); LCMS (electrospray) m/z 411.2 (M + H)+. J(1S,2S)-N-(5-(7-(dimethylamino)-6- fluoro-5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 2TFA 491

¹H NMR (400 MHz, DMSO-d₆) δ 13.49 (br s, 1H), 11.14 (s, 1H), 8.62 (d, J= 7.0 Hz, 1H), 7.79 (br s, 1H), 7.62 (d, J = 1.0 Hz, 1H), 6.91 (s, 1H),6.84 (dd, J = 1.9, 7.1 Hz, 1H), 5.08-4.80 (m, 1H), 4.08 (s, 3H), 2.23(d, J = 3.1 Hz, 3H), 2.15 (td, J = 6.9, 14.0 Hz, 1H), 1.75-1.59 (m, 1H),1.24-1.11 (m, 1H); LCMS (electrospray) m/z 398.2 (M + H)+. J(1S,2S)-2-fluoro-N-(5-(6-fluoro-7- methoxy-5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide. 2 TFA 492

¹H NMR (400 MHz, DMSO-d₆) δ 13.84 (br s, 1H), 11.16 (s, 1H), 8.66 (d, J= 7.2 Hz, 1H), 7.94 (s, 1H), 7.77-7.72 (m, 1H), 6.96 (s, 1H), 6.91 (dd,J = 1.9, 7.1 Hz, 1H), 5.09-4.77 (m, 1H), 4.16 (d, J = 1.5 Hz, 3H), 2.15(td, J = 6.9, 13.7 Hz, 1H), 1.74-1.59 (m, 1H), 1.24-1.10 (m, 1H); LCMS(electrospray) m/z 418.2 (M + H)+. J (1S,2S)-N-(5-(5-chloro-6-fluoro-7-methoxy-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA 493

¹H NMR (400 MHz, DMSO-d₆) δ 13.80 (br s, 1H), 11.17 (s, 1H), 8.66 (d, J= 7.1 Hz, 1H), 7.94 (br s, 1H), 7.75 (s, 1H), 6.95 (s, 1H), 6.92 (dd, J= 1.8, 7.2 Hz, 1H), 5.13-4.78 (m, 1H), 4.39 (br d, J = 6.5 Hz, 2H),2.21-2.09 (m, 1H), 1.74-1.60 (m, 1H), 1.41 (t, J = 7.0 Hz, 3H),1.24-1.12 (m, 1H); LCMS (electrospray) m/z 432.4 (M + H)+. J(1S,2S)-N-(5-(5-chloro-7-ethoxy-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 494

¹H NMR (400 MHz, DMSO-d₆) δ 11.14 (s, 1H), 8.60 (d, J = 7.1 Hz, 1H),7.88 (s, 1H), 7.68 (dd, J = 0.8, 1.8 Hz, 1H), 6.92 (s, 1H), 6.89 (dd, J= 2.0, 7.1 Hz, 1H), 5.08-4.78 (m, 1H), 3.17 (d, J = 2.8 Hz, 3H), 2.14(td, J = 7.0, 13.9 Hz, 1H), 1.74-1.58 (m, 1H), 1.17 (tdd, J = 6.3, 9.0,12.3 Hz, 1H); LCMS (electrospray) m/z 417.4 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7- (methylamino)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 2TFA 495

¹H NMR (400 MHz, DMSO-d₆) δ 13.44 (br d, J = 2.8 Hz, 1H), 11.18 (s, 1H),8.65 (d, J = 7.1 Hz, 1H), 8.17 (s, 1H), 7.90 (br s, 1H), 7.77-7.68 (m,1H), 6.95 (s, 1H), 6.91 (dd, J = 2.0, 7.1 Hz, 1H), 5.06- 4.83 (m, 1H),3.30 (br s, 4H), 2.57 (br s, 4H), 2.28 (s, 3H), 2.19-2.10 (m, 1H),1.73-1.60 (m, 1H), 1.25-1.11 (m, 1H); LCMS (electrospray) m/z 486.2 (M +H)+. J (1S,2S)-N-(5-(5-chloro-6-fluoro-7-(4-methylpiperazin-1-yl)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 1 FA 496

¹H NMR (400 MHz, DMSO-d₆) δ 11.16 (1 H, s) 8.62 (1 H, d, J = 7.20 Hz)7.89 (1 H, br s) 7.70 (1 H, d, J = 1.00 Hz) 7.04-6.79 (2 H, m) 5.07-4.70(1 H, m) 2.15 (1 H, dt, J = 13.85, 7.02 Hz) 1.73-1.61 (1 H, m) 1.25-1.16(4 H, m); LCMS (electrospray) m/z 431.0 (M + H)+. J(1S,2S)-N-(5-(5-chloro-7-(ethylamino)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA 497

¹H NMR (400 MHz, DMSO-d₆) δ 13.78-13.23 (1 H, m) 11.18 (1 H, s) 8.66 (1H, d, J = 7.20 Hz) 7.90 (1 H, s) 7.83-7.73 (1 H, m) 7.05-6.90 (2 H, m)5.10-4.83 (1 H, m) 3.30 (4 H, q, J = 6.65 Hz) 2.15 (1 H, dt, J = 13.77,6.98 Hz) 1.77-1.61 (1 H, m) 1.27-1.14 (1 H, m) 1.02 (6 H, t, J = 7.09Hz); LCMS (electrospray) m/z 459.0 (M + H)+. J(1S,2S)-N-(5-(5-chloro-7-(diethylamino)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA 498

¹H NMR (400 MHz, DMSO-d₆) δ 13.53 (br s, 1H), 11.16 (s, 1H), 8.65 (d, J= 7.2 Hz, 1H), 7.90 (br s, 1H), 7.74 (d, J = 1.0 Hz, 1H), 6.95 (s, 1H),6.93- 6.88 (m, 1H), 5.05-4.83 (m, 1H), 3.92-3.76 (m, 4H), 3.30-3.21 (m,4H), 2.14 (td, J = 6.9, 13.9 Hz, 1H), 1.73-1.61 (m, 1H), 1.18 (tdd, J =6.2, 9.1, 12.3 Hz, 1H); LCMS (electrospray) m/z 473.3 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-morpholino-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA 499

¹H NMR (400 MHz, DMSO-d₆) δ 13.24 (br s, 1H), 11.14 (s, 1H), 8.61 (d, J= 7.2 Hz, 1H), 7.89 (br s, 1H), 7.69 (d, J = 1.0 Hz, 1H), 6.92 (s, 1H),6.88 (dd, J = 2.0, 7.1 Hz, 1H), 5.07-4.82 (m, 1H), 3.72 (br s, 4H),2.19-2.10 (m, 1H), 1.99-1.90 (m, 4H), 1.74-1.61 (m, 1H), 1.23-1.12 (m,1H); LCMS (electrospray) m/z 457.3 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7- (pyrrolidin-1-yl)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 2TFA 500

¹H NMR (400 MHz, DMSO-d₆) δ 13.61 (br s, 1H), 11.17 (s, 1H), 8.81 (br s,2H), 8.67 (d, J = 7.1 Hz, 1H), 7.94 (br s, 1H), 7.73 (d, J = 1.0 Hz,1H), 6.97 (s, 1H), 6.90 (dd, J = 1.9, 7.2 Hz, 1H), 5.08-4.81 (m, 1H),3.62-3.40 (m, 8H), 2.22-2.09 (m, 1H), 1.74-1.59 (m, 1H), 1.26-1.11 (m,1H); LCMS (electrospray) m/z 472.3 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7- (piperazin-1-yl)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 3TFA 501

¹H NMR (400 MHz, DMSO-d₆) δ13.10 (br s, 1H), 11.14 (s, 1H), 8.61 (d, J =7.1 Hz, 1H), 7.88 (br s, 1H), 7.68 (d, J = 0.9 Hz, 1H), 6.92 (s, 1H),6.88 (dd, J = 1.9, 7.1 Hz, 1H), 5.16-4.74 (m, 1H), 4.51-4.25 (m, 4H),2.35 (quin, J = 7.3 Hz, 2H), 2.14 (td, J = 6.9, 13.9 Hz, 1H), 1.76-1.57(m, 1H), 1.29-1.06 (m, 1H); LCMS (electrospray) m/z 443.3 (M + H)+. J(1S,2S)-N-(5-(7-(azetidin-1-yl)-5-chloro-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 502

¹H NMR (400 MHz, DMSO-d₆) δ 13.45 (br s, 1H), 11.17 (s, 1H), 9.37 (br s,1H), 8.66 (d, J = 7.1 Hz, 1H), 7.90 (br s, 1H), 7.74 (d, J = 1.0 Hz,1H), 6.96 (s, 1H), 6.92 (dd, J = 2.0, 7.1 Hz, 1H), 5.05-4.84 (m, 1H),3.13 (br s, 2H), 2.92 (d, J = 2.4 Hz, 3H), 2.72 (s, 3H), 2.70 (s, 3H),2.14 (br d, J = 7.1 Hz, 1H), 2.02 (br s, 4H), 1.73-1.62 (m, 1H), 1.48(br s, 4H), 1.23-1.13 (m, 1H); LCMS(electrospray) m/z542.3 (M + H+). J(1S,2S)-N-(5-(5-chloro-7-((4- (dimethylamino)cyclohexyl)(methyl)amino)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 3 TFA 503

¹H NMR (400 MHz, DMSO-d₆) δ 13.94-13.16 (m, 1H), 11.18 (s, 1H), 8.66 (d,J = 7.2 Hz, 1H), 7.90 (s, 1H), 7.82-7.71 (m, 1H), 7.84-7.70 (m, 1H),7.04-6.85 (m, 2H), 5.09-4.82 (m, 1H), 3.44- 3.32 (m, 1H), 3.24-3.06 (m,1H), 2.95-2.81 (m, 3H), 2.23-2.07 (m, 1H), 1.90-1.76 (m, 3H), 1.74- 1.34(m, 6H), 1.26-1.07 (m, 3H); LCMS(electrospray) m/z 515.2 (M + H+). J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-((4-hydroxycyclohexyl)(methyl)amino)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 3 TFA 504

¹H NMR (400 MHz, DMSO-d₆) δ 13.44 (br s, 1H), 11.17 (s, 1H), 8.66 (d, J= 7.1 Hz, 1H), 8.37 (br s, 2H), 7.91 (s, 1H), 7.74 (d, J = 1.0 Hz, 1H),6.96 (s, 1H), 6.92 (dd, J = 2.0, 7.2 Hz, 1H), 5.07-4.82 (m, 1H), 3.10(br s, 1H), 2.91 (d, J = 2.6 Hz, 3H), 2.56- 2.52 (m, 5H), 2.15 (td, J =6.9, 13.5 Hz, 1H), 2.06 (br d, J = 9.9 Hz, 2H), 1.99 (br d, J = 11.5 Hz,2H), 1.72-1.61 (m, 1H), 1.54-1.44 (m, 2H), 1.38-1.26 (m, 2H), 1.21-1.14(m, 1H); LCMS(electrospray) m/z 528.3 (M + H+). J(1S,2S)-N-(5-(5-chloro-6-fluoro-7- (methyl((1R,4R)-4-(methylamino)cyclohexyl)amino)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 3 TFA 505

¹H NMR (400 MHz, DMSO-d₆) δ 13.35 (br s, 1H), 11.18 (s, 1H), 8.67 (d, J= 7.2 Hz, 1H), 8.33 (br s, 2H), 7.94 (s, 1H), 7.79-7.75 (m, 1H), 6.97(s, 1H), 6.94 (dd, J = 2.0, 7.1 Hz, 1H), 5.06-4.84 (m, 1H), 3.08 (br s,1H), 2.85 (s, 3H), 2.57 (t, J = 5.4 Hz, 3H), 2.54-2.52 (m, 2H), 2.15(td, J = 7.2, 14.0 Hz, 1H), 1.83 (br s, 4H), 1.72-1.56 (m, 5H),1.23-1.13 (m, 1H); LCMS(electrospray) m/z 528.3 (M + H+). J(1S,2S)-N-(5-(5-chloro-6-fluoro-7- (methyl((1S,4S)-4-(methylamino)cyclohexyl)amino)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 3 TFA 506

¹H NMR (400 MHz, DMSO-d₆) δ 13.33 (br s, 1H), 11.11 (s, 1H), 8.58 (d, J= 7.0 Hz, 1H), 7.71 (s, 1H), 7.57 (d, J = 0.9 Hz, 1H), 6.88 (s, 1H),6.84-6.79 (m, 2H), 5.07-4.80 (m, 1H), 3.99 (s, 3H), 2.35 (s, 3H), 2.14(td, J = 7.1, 14.0 Hz, 1H), 1.73-1.61 (m, 1H), 1.17 (tdd, J = 6.2, 8.9,12.3 Hz, 1H); LCMS(electrospray) m/z 380.2 (M + H+). J(1S,2S)-2-fluoro-N-(5-(7-methoxy-5- methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropane-1- carboxamide. 2 TFA 507

¹H NMR (400 MHz, DMSO-d₆) δ 13.76 (br s, 1H), 11.18 (s, 1H), 8.66 (d, J= 7.1 Hz, 1H), 7.94 (br s, 1H), 7.75 (d, J = 1.0 Hz, 1H), 6.95 (s, 1H),6.92 (dd, J = 2.0, 7.1 Hz, 1H), 5.06-4.83 (m, 1H), 4.33 (br s, 2H),4.27-4.20 (m, 1H), 3.81-3.74 (m, 1H), 3.69 (dt, J = 6.1, 7.6 Hz, 1H),2.18-2.10 (m, 1H), 2.07- 1.98 (m, 1H), 1.92-1.81 (m, 2H), 1.80-1.73 (m,1H), 1.72-1.62 (m, 1H), 1.18 (tdd, J = 6.2, 9.1, 12.3 Hz, 1H);LCMS(electrospray) m/z 488.2 (M + H+). J(1S,2S)-N-(5-(5-chloro-6-fluoro-7- ((tetrahydrofuran-2-yl)methoxy)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 508

¹H NMR (400 MHz, DMSO-d₆) δ 13.30 (br s, 1H), 11.16 (s, 1H), 8.62 (br d,J = 7.1 Hz, 1H), 8.45 (br s, 2H), 7.85 (s, 1H), 7.70 (s, 1H), 6.93 (s,1H), 6.89 (dd, J = 2.0, 7.1 Hz, 1H), 5.27 (br d, J = 8.9 Hz, 1H),5.05-4.83 (m, 1H), 3.60 (br s, 1H), 2.99 (br s, 1H), 2.58 (br t, J = 5.2Hz, 3H), 2.52 (br s, 1H), 2.18- 2.12 (m, 1H), 2.08 (br d, J = 9.8 Hz,4H), 1.72-1.62 (m, 1H), 1.45-1.32 (m, 4H), 1.23-1.14 (m, 1H); J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-((4-(methylamino)cyclohexyl)amino)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 3 TFA 509

¹H NMR (400 MHz, DMSO-d₆) δ 13.47 (br s, 1H), 11.16 (s, 1H), 8.62 (d, J= 7.1 Hz, 1H), 7.79 (s, 1H), 7.64 (d, J = 0.9 Hz, 1H), 6.91 (s, 1H),6.85 (dd, J = 2.0, 7.1 Hz, 1H), 5.10-4.81 (m, 1H), 4.31 (br d, J = 6.8Hz, 2H), 2.23 (d, J = 3.1 Hz, 3H), 2.14 (td, J = 6.9, 13.9 Hz, 1H),1.73-1.61 (m, 1H), 1.39 (t, J = 7.0 Hz, 3H), 1.17 (tdd, J = 6.2, 9.1,12.3 Hz, 1H); LCMS(electrospray) m/z 412.2 (M + H+). J(1S,2S)-N-(5-(7-ethoxy-6-fluoro-5- methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA 510

¹H NMR (400 MHz, DMSO-d₆) δ 13.16-12.81 (m, 1H), 11.15 (s, 1H), 8.61 (d,J = 7.1 Hz, 1H), 7.84 (s, 1H), 7.72-7.66 (m, 1H), 6.95-6.86 (m, 2H),6.00-5.59 (m, 2H), 5.17-4.76 (m, 1H), 2.21- 2.09 (m, 1H), 1.76-1.59 (m,1H), 1.43-1.36 (m, 1H), 1.26-1.11 (m, 1H); LCMS(electrospray) m/z 403.1(M + H+). J (1S,2S)-N-(5-(7-amino-5-chloro-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 511

¹H NMR (400 MHz, DMSO-d₆) δ 13.28 (s, 1H), 11.12 (s, 1H), 8.58 (d, J =7.1 Hz, 1H), 7.70 (d, J = 1.2 Hz, 1H), 7.57 (dd, J = 0.9, 1.7 Hz, 1H),6.87 (s, 1H), 6.84-6.79 (m, 2H), 5.05-4.83 (m, 1H), 4.27 (q, J = 7.0 Hz,2H), 2.34 (s, 3H), 2.19-2.09 (m, 1H), 1.72-1.61 (m, 1H), 1.46 (t, J =7.0 Hz, 3H), 1.17 (tdd, J = 6.3, 9.0, 12.3 Hz, 1H); LCMS(electrospray)m/z 393.9 (M + H+). J (1S,2S)-N-(5-(7-ethoxy-5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 512

¹H NMR (400 MHz, DMSO-d₆) δ 13.27 (br s, 1H), 11.15 (s, 1H), 9.49 (br s,1H), 8.62 (d, J = 7.1 Hz, 1H), 7.88 (br s, 1H), 7.69 (d, J = 1.0 Hz,1H), 6.93 (s, 1H), 6.90 (dd, J = 2.0, 7.2 Hz, 1H), 5.33 (br s, 1H),5.11-4.77 (m, 1H), 3.19 (br d, J = 9.0 Hz, 1H), 2.77 (s, 3H), 2.76 (s,3H), 2.52 (d, J = 2.0 Hz, 1H), 2.12 (br d, J = 11.7 Hz, 3H), 2.04 (br d,J = 10.8 Hz, 2H), 1.72-1.61 (m, 1H), 1.61-1.51 (m, 2H), 1.46- 1.32 (m,2H), 1.17 (tdd, J = 6.2, 9.0, 12.4 Hz, 1H); LCMS(electrospray) m/z 528.3(M + H+). J (1S,2S)-N-(5-(5-chloro-7-((4-(dimethylamino)cyclohexyl)amino)-6- fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 3 TFA 513

¹H NMR (400 MHz, DMSO-d₆) δ 13.49 (s, 1H), 11.18 (s, 1H), 8.66 (d, J =7.2 Hz, 1H), 7.76 (s, 1H), 7.64 (s, 1H), 6.93 (s, 1H), 6.82 (d, J = 7.2Hz, 1H), 5.04-4.84 (m, 1H), 2.69-2.62 (m, 2H), 2.50 (s, 3H), 2.16-2.12(m, 1H), 1.70-1.63 (m, 1H), 1.28- 1.12 (m, 1H), 1.12-1.08 (m, 3H); LCMS(electrospray) m/z 428.1 (M + H)+. J (1S,2S)-N-(5-(5-ethyl-6-fluoro-7-(methylthio)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide dihydrochloride. 2 HCl 514

¹H NMR (400 MHz, DMSO-d₆) δ 13.63-13.08 (m, 1H), 11.19 (s, 1H), 8.67(td, J = 1.0, 7.1 Hz, 1H), 8.03-7.86 (m, 1H), 7.83-7.56 (m, 4H), 7.06-6.86 (m, 2H), 5.14-4.81 (m, 2H), 3.24-3.15 (m, 1H), 2.95-2.84 (m, 4H),2.15 (td, J = 7.0, 13.9 Hz, 1H), 2.02-1.91 (m, 2H), 1.86-1.74 (m, 2H),1.73- 1.45 (m, 4H), 1.41-1.28 (m, 1H), 1.25-1.12 (m, 1H);LCMS(electrospray) m/z 514.1 (M + H+). J (1S,2S)-N-(5-7-((4-aminocyclohexyl)(methyl)amino)-5- chloro-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 3TFA 515

¹H NMR (400 MHz, DMSO-d₆) δ 13.32 (br d, J = 13.8 Hz, 1H), 11.16 (s,1H), 8.63 (br d, J = 6.9 Hz, 1H), 7.95-7.60 (m, 5H), 6.99-6.79 (m, 2H),5.35- 4.78 (m, 2H), 4.09-3.63 (m, 1H), 4.05-3.45 (m, 1H), 3.24-2.98 (m,3H), 2.15 (td, J = 6.9, 13.7 Hz, 1H), 2.09-1.93 (m, 2H), 1.77 (br s,3H), 1.72- 1.61 (m, 1H), 1.53-1.34 (m, 2H), 1.26-1.14 (m, 1H);LCMS(electrospray) m/z 500.4 (M + H+). J (1S,2S)-N-(5-(7-((4-aminocyclohexyl)amino)-5-chloro-6- fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 3 TFA 516

¹H NMR (400 MHz, DMSO-d₆) δ 14.54-12.40 (m, 1H), 11.16 (s, 1H), 8.62 (d,J = 7.3 Hz, 1H), 7.98-7.77 (m, 1H), 7.71 (br s, 1H), 7.02-6.86 (m, 2H),6.84-6.66 (m, 1H), 5.07-4.82 (m, 1H), 3.47 (br s, 2H), 3.26 (br s, 1H),2.15 (td, J = 6.8, 13.6 Hz, 1H), 1.99 (br d, J = 10.3 Hz, 1H), 1.82 (brd, J = 10.4 Hz, 1H), 1.74-1.62 (m, 4H), 1.55 (br d, J = 10.4 Hz, 1H),1.39 (d, J = 5.1 Hz, 9H), 1.36-1.11 (m, 3H); LCMS(electrospray) m/z600.1 (M + H+). J tert-butyl (4-((5-chloro-6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1-carboxamido)pyrazolo[1,5-a]pyridin-5-yl)- 1H-indazol-7-yl)amino)cyclohexyl)carbamate. 2 TFA 517

¹H NMR (400 MHz, DMSO-d₆) δ 13.70-12.88 (m, 1H), 11.24-11.06 (m, 1H),8.71-8.53 (m, 1H), 7.93-7.64 (m, 2H), 7.05-6.57 (m, 2H), 5.10-4.69 (m,1H), 3.92-3.72 (m, 3H), 2.27-2.08 (m, 1H), 1.81-1.45 (m, 8H), 1.34-1.09(m, 2H); LCMS(electrospray) m/z 501.1 (M + H+). J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-((4-hydroxycyclohexyl)amino)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 2TFA 518

¹H NMR (400 MHz, DMSO-d₆) δ 13.15 (br s, 1H), 11.15 (s, 1H), 8.62 (d, J= 7.1 Hz, 1H), 7.68 (br s, 1H), 7.62 (s, 1H), 6.91 (s, 1H), 6.83 (dd, J= 1.8, 7.1 Hz, 1H), 5.06-4.82 (m, 1H), 3.26 (br d, J = 6.1 Hz, 4H), 2.61(br d, J = 7.1 Hz, 2H), 2.19-2.10 (m, 1H), 1.74-1.60 (m, 1H), 1.21-1.14(m, 1H), 1.10 (t, J = 7.4 Hz, 3H), 0.99 (t, J = 7.1 Hz, 6H);LCMS(electrospray) m/z 453.4(M + H+). J(1S,2S)-N-(5-(7-(diethylamino)-5-ethyl-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA 519

¹H NMR (400 MHz, DMSO-d₆) δ 13.99-12.38 (m, 1H), 11.14 (s, 1H), 8.61 (d,J = 7.1 Hz, 1H), 7.68 (s, 1H), 7.58 (d, J = 0.9 Hz, 1H), 6.90 (s, 1H),6.79 (dd, J = 1.9, 7.0 Hz, 1H), 5.11-4.76 (m, 1H), 2.97 (s, 3H), 2.97(s, 3H), 2.65-2.53 (m, 2H), 2.14 (td, J = 6.9, 13.8 Hz, 1H), 1.75-1.60(m, 1H), 1.22- 1.14 (m, 1H), 1.10 (t, J = 7.4 Hz, 3H);LCMS(electrospray) m/z425.2 (M + H+). J(1S,2S)-N-(5-(7-(dimethylamino)-5-ethyl-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA 520

¹H NMR (400 MHz, DMSO-d₆) δ 13.79 (br s, 1H), 11.18 (s, 1H), 8.68 (d, J= 7.2 Hz, 1H), 7.99 (br s, 1H), 7.80 (d, J = 0.7 Hz, 1H), 6.98 (s, 1H),6.96 (dd, J = 1.9, 7.2 Hz, 1H), 5.06-4.82 (m, 1H), 3.53 (t, J = 6.7 Hz,2H), 3.12-3.04 (m, 2H), 2.15 (td, J = 7.1, 13.8 Hz, 1H), 1.73-1.61 (m,1H), 1.18 (tdd, J = 6.2, 9.1, 12.3 Hz, 1H); LCMS(electrospray) m/z 464(M + H+). J (1S,2S)-N-(5-(5-chloro-6-fluoro-7-((2-hydroxyethyl)thio)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 521

¹H NMR (400 MHz, DMSO-d₆) δ 13.62 (s, 1H), 11.17 (s, 1H), 8.66 (d, J =7.1 Hz, 1H), 8.07 (d, 1H), 7.78 (s, 1H), 7.65 (d, 1H), 6.94 (s, 1H),6.83 (dd, 1H), 5.08-4.83 (m, 1H), 3.64 (s, 2H), 2.63 (d, 2H), 2.60 (d,3H), 2.20-2.11 (m, 1H), 1.75-1.61 (m, 1H), 1.24-1.15 (m, 1H), 1.11 (t,3H); LCMS(electrospray) m/z 485.2 (M + H+). J(1S,2S)-N-(5-(5-ethyl-6-fluoro-7-((2- (methylamino)-2-oxoethyl)thio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide bis(2,2,2-trifluoroacetate). 2 TFA522

¹H NMR (400 MHz, DMSO-d₆) δ 13.72-13.26 (m, 1H), 11.18 (s, 1H), 8.66 (d,J = 7.1 Hz, 1H), 7.78 (s, 1H), 7.64 (d, J = 0.8 Hz, 1H), 6.95 (s, 1H),6.82 (dd, J = 1.9, 7.1 Hz, 1H), 5.13-4.76 (m, 1H), 3.97 (s, 2H), 3.02(s, 3H), 2.83 (s, 3H), 2.66-2.59 (m, 2H), 2.19-2.08 (m, 1H), 1.74-1.61(m, 1H), 1.23-1.15 (m, 1H), 1.11 (t, J = 7.4 Hz, 3H); LCMS(electrospray)m/z 499.4 (M + H+). J (1S,2S)-N-(5-7-((2-(dimethylamino)-2-oxoethyl)thio)-5-ethyl-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide bis(2,2,2-trifluoroacetate). 2 TFA523

¹H NMR (400 MHz, DMSO-d₆) δ 13.46 (s, 1H), 11.16 (s, 1H), 8.65 (d, J =7.1 Hz, 1H), 7.84 (s, 1H), 7.68 (d, J = 0.7 Hz, 1H), 6.93 (s, 1H), 6.88(dd, J = 2.0, 7.1 Hz, 1H), 5.08-4.81 (m, 2H), 3.51 (t, J = 6.9 Hz, 2H),3.01 (br t, J = 6.8 Hz, 2H), 2.24 (d, J = 2.9 Hz, 3H), 2.15 (td, J =6.9, 14.0 Hz, 1H), 1.73- 1.61 (m, 1H), 1.17 (tdd, J = 6.2, 9.0, 12.3 Hz,1H); LCMS(electrospray) m/z 444.1 (M + H+). J(1S,2S)-2-fluoro-N-(5-(6-fluoro-7-((2-hydroxyethyl)thio)-5-methyl-1H-indazol- 4-yl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropane-1-carboxamide. 2 TFA 524

¹H NMR (400 MHz, DMSO-d₆) δ 11.13 (s, 1H), 8.58 (d, J = 7.1 Hz, 1H),7.67 (s, 1H), 7.55 (d, J = 0.8 Hz, 1H), 6.88 (s, 1H), 6.78 (dd, J = 1.9,7.1 Hz, 1H), 5.06-4.82 (m, 1H), 3.50 (q, J = 7.0 Hz, 2H), 2.60 (br d, J= 7.6 Hz, 2H), 2.14 (td, J = 7.2, 13.9 Hz, 1H), 1.74-1.59 (m, 1H),1.22-1.07 (m, 7H); LCMS(electrospray) m/z 425.2 (M + H+). J(1S,2S)-N-(5-(5-ethyl-7-(ethylamino)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA 525

¹H NMR (400 MHz, DMSO-d₆) δ 13.48-12.86 (m, 1H), 11.15 (s, 1H), 8.62 (d,J = 7.0 Hz, 1H), 7.68 (s, 1H), 7.60 (d, J = 0.9 Hz, 1H), 6.91 (s, 1H),6.81 (dd, J = 1.9, 7.0 Hz, 1H), 5.08-4.79 (m, 1H), 3.23 (q, J = 7.0 Hz,2H), 2.95 (d, J = 1.6 Hz, 3H), 2.60 (br d, J = 7.1 Hz, 2H), 2.18-2.10(m, 1H), 1.72-1.61 (m, 1H), 1.20-1.14 (m, 1H), 1.12-1.04 (m, 6H);LCMS(electrospray) m/z 439.2 (M + H+). J (1S,2S)-N-(5-(5-ethyl-7-(ethyl(methyl)amino)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 526

¹H NMR (400 MHz, DMSO-d₆) δ 13.70-13.32 (m, 1H), 13.12-12.20 (m, 1H),11.17 (s, 1H), 8.65 (d, J = 7.1 Hz, 1H), 7.79 (s, 1H), 7.65 (d, J = 0.9Hz, 1H), 6.94 (s, 1H), 6.83 (dd, J = 2.0, 7.1 Hz, 1H), 5.07-4.82 (m,1H), 3.77 (br s, 2H), 2.63 (br d, J = 6.8 Hz, 2H), 2.21-2.09 (m, 1H),1.74-1.61 (m, 1H), 1.24-1.14 (m, 1H), 1.10 (t, J = 7.4 Hz, 3H);LCMS(electrospray) m/z 472.1 (M + H+). J2-((5-ethyl-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)pyrazolo[1,5-a]pyridin-5-yl)- 1H-indazol-7-yl)thio)aceticacid. 2 TFA 527

¹H NMR (400 MHz, DMSO-d₆) δ 13.64-13.45 (m, 1H), 11.24-11.12 (m, 1H),8.72-8.62 (m, 1H), 8.02-7.73 (m, 4H), 7.03-6.89 (m, 2H), 5.13-4.83 (m,1H), 2.88 (br d, J = 17.4 Hz, 2H), 2.08 (s, 5H), 2.04-1.93 (m, 2H),1.75-1.58 (m, 3H), 1.28-1.18 (m, 3H); LCMS(electrospray) m/z 500.1 (M +H+). J (1S,2S)-N-(5-(7-((3- aminocyclopentyl)(methyl)amino)-5-chloro-6-fluoro-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 528

¹H NMR (400 MHz, METHANOL-d₄) δ 8.75 (s, 1H), 7.88 (s, 1H), 7.82-7.76(m, 1H), 7.74-7.68 (m, 1H), 2.19-2.11 (m, 1H), 1.92-1.81 (m, 1H),1.35-1.22 (m, 2H); LCMS(electrospray) m/z 404.1 (M + H+). J(1S,2S)-N-(5-(5-chloro-6-fluoro-7- hydroxy-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 2 TFA 529

¹H NMR (400 MHz, DMSO-d₆) δ 13.68 (s, 1H), 11.16 (s, 1H), 8.63 (d, J =7.1 Hz, 1H), 7.88 (d, J = 1.3 Hz, 1H), 7.68 (d, J = 1.0 Hz, 1H), 6.94(s, 1H), 6.90 (dd, J = 1.8, 7.1 Hz, 1H), 5.07-4.82 (m, 1H), 2.54 (s,3H), 2.28 (s, 3H), 2.19-2.10 (m, 1H), 1.79- 1.57 (m, 1H), 1.26-1.12 (m,1H); LCMS(electrospray) m/z 446.0 (M + H+). J(1S,2S)-2-fluoro-N-(5-(6-fluoro-5,7- bis(methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide. 2 TFA 530

¹H NMR (400 MHz, CHLOROFORM-d) δ 13.40 (br s, 1H), 11.15 (s, 1H), 8.62(d, J = 7.1 Hz, 1H), 7.81 (s, 1H), 7.67 (dd, J = 0.7, 1.7 Hz, 1H), 7.52(dd, J = 0.9, 9.3 Hz, 1H), 6.93 (s, 1H), 6.90 (dd, J = 1.8, 7.1 Hz, 1H),5.06-4.82 (m, 1H), 2.26 (s, 3H), 2.15 (td, J = 7.0, 13.9 Hz, 1H),1.75-1.61 (m, 1H), 1.21-1.14 (m, 1H); LCMS(electrospray) m/z 400.1 (M +H+). J (1S,2S)-2-fluoro-N-(5-(6-fluoro-5- (methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide 531

¹H NMR (400 MHz, DMSO-d₆) δ 13.48 (s, 1H), 11.16 (s, 1H), 8.63 (d, J =6.8 Hz, 1H), 7.72 (s, 1H), 7.61 (s, 1H), 6.92 (s, 1H), 6.81 (dd, J =7.2, 2.0 Hz, 1H), 5.04-4.85 (m, 1H), 4.34-4.29 (m, 2H), 2.64- 2.60 (m,2H), 2.17-2.13 (m, 1H), 1.75-1.65 (m, 1H), 1.40 (t, J = 7.2 Hz, 3H),1.19-1.15 (m, 1H), 1.12 (t, J = 7.2 Hz, 3H); LCMS(electrospray) m/z426.2 (M + H+). J (1S,2S)-N-(5-(7-ethoxy-5-ethyl-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 532

¹H NMR (400 MHz, CHLOROFORM-d) δ 8.46- 8.41 (m, 1 H), 8.37 (d, J = 7.09Hz, 1 H), 7.80-7.74 (m, 1 H), 7.45 (d, J = 0.86 Hz, 1 H), 7.09 (s, 1 H),6.73 (dd, J = 7.03, 1.90 Hz, 1 H), 5.00-4.72 (m, 1 H), 2.81-2.64 (m, 2H), 2.01-1.94 (m, 1 H), 1.92- 1.89 (m, 1 H), 1.28-1.25 (m, 1 H), 1.18(t, J = 7.46 Hz, 3 H); LCMS(electrospray) m/z 400.0 (M + H+). J(1S,2S)-N-(5-(5-ethyl-6,7-difluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 2 TFA 533

¹H NMR (400 MHz, DMSO-d₆) δ 11.18 (s, 1H), 8.67 (d, J = 7.0 Hz, 1H),7.91 (s, 1H), 7.71 (s, 1H), 6.96 (s, 1H), 6.89 (dd, J = 1.9, 7.1 Hz,1H), 5.15- 4.65 (m, 1H), 3.13 (s, 3H), 2.24 (d, J = 2.8 Hz, 3H), 2.15(td, J = 7.0, 14.1 Hz, 1H), 1.76-1.58 (m, 1H), 1.26-1.10 (m, 1H);LCMS(electrospray) m/z 429.11 (M + H+). J(1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl-7-(methylsulfinyl)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropane-1-carboxamide 534

¹H NMR (400 MHz, DMSO-d₆) δ 13.39 (br s, 1H), 14.04-12.74 (m, 1H), 11.15(s, 1H), 8.63 (d, J = 7.1 Hz, 1H), 7.80 (s, 1H), 7.64 (d, J = 0.9 Hz,1H), 7.29 (dd, J = 2.0, 7.3 Hz, 1H), 6.96-6.90 (m, 1H), 6.86 (dd, J =1.8, 7.1 Hz, 1H), 5.06-4.83 (m, 1H), 4.30 (br t, J = 4.9 Hz, 2H), 3.78(t, J = 5.1 Hz, 2H), 2.24 (d, J = 3.1 Hz, 3H), 2.20-2.08 (m, 1H), 1.75-1.58 (m, 1H), 1.25-1.13 (m, 1H); LCMS(electrospray) m/z 428.0 (M + H+).J (1S,2S)-2-fluoro-N-(5-(6-fluoro-7-(2-hydroxyethoxy)-5-methyl-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropane-1-carboxamide. TFA 535

¹H NMR (400 MHz, METHANOL-d₄) δ 8.41 (d, J = 7.1 Hz, 1H), 7.66 (s, 1H),7.44 (s, 1H), 6.83 (s, 1H), 6.74 (dd, J = 1.7, 7.1 Hz, 1H), 4.86 (td, J= 3.1, 6.3 Hz, 1H), 4.69 (dt, J = 3.9, 6.2 Hz, 1H), 4.46- 4.38 (m, 2H),4.33-4.25 (m, 2H), 3.89-3.80 (m, 1H), 2.20-2.16 (m, 1H), 2.18 (d, J =3.2 Hz, 2H), 2.00 (td, J = 6.9, 13.8 Hz, 1H), 1.78-1.62 (m, 1H),1.19-1.04 (m, 1H); LCMS(electrospray) m/z 471.1 (M + H+). J2-((6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)pyrazolo[1,5-a]pyridin-5-yl)-5-methyl-1H-indazol-7-yl)oxy)ethyl carbamate 536

¹H NMR (400 MHz, DMSO-d₆) δ 11.19 (s, 1H), 8.67 (d, J = 7.2 Hz, 1H),7.67 (s, 1H), 6.96 (s, 1H), 6.87 (s, 1H), 6.79 (dd, J = 2.0, 7.2 Hz,1H), 5.08- 4.79 (m, 1H), 2.19-2.08 (m, 1H), 1.74-1.59 (m, 1H), 1.28-1.09(m, 2H); LCMS(electrospray) m/z 406.2 (M + H+). J(1S,2S)-N-(5-(5-chloro-6,7-difluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 1 TFA 537

¹H NMR (400 MHz, DMSO-d₆) δ 13.31 (br s, 1H), 11.27-11.11 (m, 1H), 10.14(s, 1H), 8.68 (d, J = 7.1 Hz, 1H), 7.91 (s, 1H), 7.80 (d, J = 0.9 Hz,1H), 6.97 (s, 1H), 6.95 (dd, J = 1.9, 7.2 Hz, 1H), 5.09- 4.82 (m, 1H),2.18 (s, 3H), 2.16-2.10 (m, 1H), 1.75-1.61 (m, 1H), 1.18 (ddd, J = 2.7,6.1, 12.5 Hz, 1H); LCMS(electrospray) m/z 445.2 (M + H+). J(1S,2S)-N-(5-(7-acetamido-5-chloro-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide. 1 TFA 538

¹H NMR (400 MHz, DMSO-d₆) δ 13.73 (br s, 1H), 11.22 (s, 1H), 8.72 (d, J= 7.0 Hz, 1H), 8.06 (s, 1H), 7.83 (d, J = 1.0 Hz, 1H), 7.01 (s, 1H),6.97 (dd, J = 2.0, 7.2 Hz, 1H), 5.08-4.83 (m, 1H), 3.20 (s, 3H), 2.16(td, J = 7.0, 14.0 Hz, 1H), 1.75-1.60 (m, 1H), 1.24-1.13 (m, 1H);LCMS(electrospray) m/z 450 (M + H+). J(1S,2S)-N-(5-(5-chloro-6-fluoro-7- (methylsulfinyl)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 539

¹H NMR (400 MHz, DMSO-d₆) δ 11.15 (s, 1H), 8.62 (d, J = 7.1 Hz, 1H),7.80 (s, 1H), 7.63 (d, J = 0.7 Hz, 1H), 6.91 (s, 1H), 6.85 (dd, J = 1.9,7.2 Hz, 1H), 6.06-5.88 (m, 1H), 5.05-4.82 (m, 1H), 4.33 (br t, J = 5.4Hz, 2H), 3.62 (br t, J = 5.8 Hz, 5H), 2.94 (s, 3H), 2.23 (d, J = 3.1 Hz,3H), 2.18-2.11 (m, 1H), 1.73-1.61 (m, 1H), 1.20-1.14 (m, 1H);LCMS(electrospray) m/z 484.4 (M + H+). J(1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl-7-(2-(1-methylureido)ethoxy)-1H-indazol- 4-yl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropane-1-carboxamide. 1 TFA 540

¹H NMR (400 MHz, DMSO-d₆) δ 12.95 (s, 1H), 11.16 (s, 1H), 9.93 (s, 1H),8.64 (d, J = 7.1 Hz, 1H), 7.76 (s, 1H), 7.67 (s, 1H), 6.93 (s, 1H), 6.87(dd, J = 1.7, 7.1 Hz, 1H), 5.06-4.82 (m, 1H), 2.24 (d, J = 2.6 Hz, 3H),2.20-2.10 (m, 4H), 1.73-1.60 (m, 1H), 1.17 (tdd, J = 6.4, 9.0, 12.3 Hz,1H); LCMS(electrospray) m/z 424.15 (M + H+). J(1S,2S)-N-(5-(7-acetamido-6-fluoro-5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 541

¹H NMR (400 MHz, DMSO-d₆) δ 11.16 (s, 1H), 8.63 (d, J = 7.1 Hz, 1H),7.96 (br s, 1H), 7.66 (d, J = 1.0 Hz, 1H), 6.94 (s, 1H), 6.88 (dd, J =2.0, 7.1 Hz, 1H), 5.06-4.83 (m, 1H), 2.30 (s, 3H), 2.15 (td, J = 7.0,14.0 Hz, 1H), 1.74-1.60 (m, 1H), 1.17 (tdd, J = 6.3, 9.0, 12.3 Hz, 1H);LCMS(electrospray) m/z 418 (M + H+). J(1S,2S)-N-(5-(6,7-difluoro-5-(methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide. 1 TFA 542

¹H NMR (400 MHz, DMSO-d₆) δ 12.97 (s, 1H), 11.16 (s, 1H), 8.63 (d, J =7.2 Hz, 1H), 8.35 (s, 1H), 7.88 (s, 1H), 7.71 (s, 1H), 6.93 (s, 1H),6.89 (d, J = 7.2 Hz, 1H), 5.04-4.85 (m, 1H), 3.23 (s, 3H), 2.16- 2.12(m, 1H), 1.70-1.63 (m, 1H), 1.28-1.12 (m, 1H); LCMS (electrospray) m/z532.1 (M + H)+. J tert-butyl 2-(5-chloro-6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1-carboxamido)pyrazolo[1,5-a]pyridin-5-yl)-1H-indazol-7-yl)-1-methylhydrazine-1- carboxylate 543

¹H NMR (400 MHz, DMSO-d₆) δ 14.02-13.34 (m, 1H), 11.15 (s, 1H), 8.61 (d,J = 7.0 Hz, 1H), 7.85 (s, 1H), 7.65 (s, 1H), 6.93 (s, 1H), 6.89 (dd, J =1.8, 7.1 Hz, 1H), 5.11-4.78 (m, 1H), 4.35 (q, J = 7.0 Hz, 2H), 2.28 (s,3H), 2.19-2.12 (m, 1H), 1.68 (m, J = 3.2, 6.8, 19.9 Hz, 1H), 1.41 (t, J= 7.0 Hz, 3H), 1.26-1.11 (m, 1H); LCMS(electrospray) m/z 444.2 (M + H+).J (1S,2S)-N-(5-(7-ethoxy-6-fluoro-5- (methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 1TFA 544

¹H NMR (400 MHz, DMSO-d₆) δ 11.15 (s, 1H), 8.63 (d, J = 7.1 Hz, 1H),7.80 (s, 1H), 7.64 (d, J = 1.0 Hz, 1H), 6.91 (s, 1H), 6.85 (dd, J = 1.9,7.1 Hz, 1H), 6.28 (br s, 1H), 5.14-4.71 (m, 1H), 4.22 (t, J = 5.4 Hz,2H), 3.40 (br d, J = 4.1 Hz, 2H), 2.24 (d, J = 3.0 Hz, 3H), 2.19-2.09(m, 1H), 1.73-1.59 (m, 1H), 1.24-1.07 (m, 1H); LCMS(electrospray) m/z470.1 (M + H+). J (1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl-7-(2-ureidoethoxy)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropane-1-carboxamide. 1 TFA 545

¹H NMR (400 MHz, DMSO-d₆) δ 11.24-11.04 (m, 1H), 8.74-8.52 (m, 1H),7.85-7.75 (m, 1H), 7.64 (d, J = 0.9 Hz, 1H), 6.91 (s, 1H), 6.85 (dd, J =1.8, 7.1 Hz, 1H), 6.27-6.15 (m, 1H), 6.03-5.80 (m, 1H), 5.09-4.80 (m,1H), 4.31-4.12 (m, 2H), 3.47- 3.34 (m, 2H), 2.57 (s, 3H), 2.23 (d, J =3.1 Hz, 3H), 2.19-2.08 (m, 1H), 1.75-1.60 (m, 1H), 1.25- 1.10 (m, 1H);LCMS(electrospray) m/z 484.2 (M + H+). J(1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl-7-(2-(3-methylureido)ethoxy)-1H-indazol- 4-yl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropane-1-carboxamide. 1 TFA 546

¹H NMR (400 MHz, DMSO-d₆) δ 13.52-13.40 (m, 1H), 11.16 (s, 1H), 8.64 (d,J = 7.1 Hz, 1H), 7.85 (br s, 1H), 7.68 (s, 1H), 6.94 (s, 1H), 6.89 (dd,J = 1.6, 7.0 Hz, 1H), 5.04-4.83 (m, 1H), 4.05 (br t, J = 6.7 Hz, 2H),3.16 (br d, J = 5.5 Hz, 2H), 2.53 (br s, 3H), 2.25 (d, J = 2.7 Hz, 3H),2.17-2.13 (m, 1H), 2.04 (td, J = 2.4, 4.9 Hz, 1H), 1.68 (tdd, J = 3.3,6.6, 19.7 Hz, 1H), 1.17 (ddd, J = 2.6, 6.2, 12.3 Hz, 1H);LCMS(electrospray) m/z 501.2 (M + H+). J 2-((6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1- carboxamido)pyrazolo[1,5-a]pyridin-5-yl)-5-methyl-1H-indazol-7-yl)thio)ethyl methylcarbamate. 1 TFA 547

¹H NMR (400 MHz, DMSO-d₆) δ 13.67-13.25 (m, 1H), 11.16 (s, 1H), 9.63 (brt, J = 5.2 Hz, 1H), 8.63 (d, J = 7.1 Hz, 1H), 7.82 (s, 1H), 7.64 (d, J =0.9 Hz, 1H), 6.92 (s, 1H), 6.85 (dd, J = 1.9, 7.2 Hz, 1H), 5.07-4.83 (m,1H), 4.38 (s, 2H), 3.66 (q, J = 5.5 Hz, 3H), 2.23 (d, J = 3.1 Hz, 3H),2.15 (td, J = 7.0, 13.8 Hz, 1H), 1.75-1.61 (m, 1H), 1.18-1.29 (m, J =2.9, 6.1, 12.3 Hz, 1H); LCMS(electrospray) m/z 523.3 (M + H+). J(1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl-7-(2-(2,2,2-trifluoroacetamido)ethoxy)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide.1 TFA 548

¹H NMR (400 MHz, DMSO-d₆) δ 13.32 (s, 1H), 11.19 (s, 1H), 8.68 (d, J =7.1 Hz, 1H), 7.89 (s, 1H), 7.73 (s, 1H), 6.96 (s, 1H), 6.89 (dd, J =1.8, 7.1 Hz, 1H), 5.15-4.72 (m, 1H), 3.98 (s, 3H), 2.24 (d, J = 2.9 Hz,3H), 2.20-2.09 (m, 1H), 1.76-1.59 (m, 1H), 1.18 (ddd, J = 2.8, 6.2, 12.2Hz, 1H); LCMS(electrospray) m/z 426.2 (M + H+). J methyl6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)pyrazolo[1,5-a]pyridin-5-yl)-5-methyl-1H-indazole-7-carboxylate 549

¹H NMR (400 MHz, DMSO-d₆) δ 13.66-13.38 (m, 1H), 13.19 (br s, 1H), 11.19(s, 1H), 8.68 (d, J = 7.1 Hz, 1H), 7.85 (s, 1H), 7.72 (s, 1H), 6.96 (s,1H), 6.89 (dd, J = 1.8, 7.1 Hz, 1H), 5.07-4.84 (m, 1H), 2.24 (d, J = 3.1Hz, 3H), 2.18-2.13 (m, 1H), 1.72-1.62 (m, 1H), 1.20-1.14 (m, 1H);LCMS(electrospray) m/z 412.2 (M + H+). J 6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1- carboxamido)pyrazolo[1,5-a]pyridin-5-yl)-5-methyl-1H-indazole-7-carboxylic acid. 1 TFA 550

¹H NMR (400 MHz, DMSO-d₆) δ 11.22-11.13 (m, 1H), 8.66 (d, J = 7.1 Hz,1H), 7.95-7.87 (m, 1H), 7.72-7.70 (m, 1H), 6.96-6.93 (m, 1H), 6.92-6.89(m, 1H), 5.07-4.81 (m, 1H), 3.21 (s, 3H), 2.30- 2.25 (m, 3H), 2.25-2.23(m, 1H), 2.20-2.09 (m, 1H), 1.79 (s, 3H), 1.74-1.63 (m, 1H), 1.28-1.09(m, 1H); LCMS(electrospray) m/z 438.16 (M + H+) J(1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl-7-(N-methylacetamido)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropane-1-carboxamide. 1 TFA 551

¹H NMR (400 MHz, DMSO-d₆) δ 13.47 (br s, 1H), 11.20 (s, 1H), 8.70 (d, J= 7.1 Hz, 1H), 7.99 (s, 1H), 7.83 (d, J = 0.9 Hz, 1H), 7.03-6.95 (m,2H), 5.10- 4.82 (m, 1H), 2.22-2.09 (m, 1H), 1.79-1.60 (m, 1H), 1.26-1.11(m, 1H); LCMS(electrospray) m/z 432.2 (M + H+). J5-chloro-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)pyrazolo[1,5-a]pyridin-5-yl)- 1H-indazole-7-carboxylic acid.1 TFA 552

¹H NMR (400 MHz, DMSO-d₆) δ 14.07-13.87 (m, 1H), 11.19 (s, 1H), 8.69 (brd, J = 7.1 Hz, 1H), 8.07-8.01 (m, 1H), 7.82 (d, J = 0.7 Hz, 1H), 6.99(s, 1H), 6.97 (br d, J = 2.0 Hz, 1H), 5.05-4.83 (m, 1H), 3.23 (s, 3H),2.18-2.11 (m, 1H), 1.82 (s, 3H), 1.71-1.64 (m, 1H), 1.22-1.13 (m, 1H);LCMS(electrospray) m/z 459.2 (M + H+). J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(N- methylacetamido)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide. 1TFA 553

¹H NMR (400 MHz, DMSO-d₆) δ 12.95 (s, 1H), 11.15 (s, 1H), 8.60 (d, J =7.2 Hz, 1H), 7.77 (s, 1H), 7.68 (s, 1H), 7.42 (s, 1H), 6.91-6.88 (m,2H), 5.02 (s, 1H), 5.04-4.85 (m, 1H), 2.66 (s, 3H), 2.16- 2.12 (m, 1H),1.70-1.63 (m, 1H), 1.28-1.12 (m, 1H); LCMS (electrospray) m/z 432.1 (M +H)+. J (1S,2S)-N-(5-(5-chloro-6-fluoro-7-(2-methylhydrazineyl)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 554

¹H NMR (400 MHz, DMSO-d₆) δ 11.22 (s, 1H), 8.71 (d, J = 7.1 Hz, 1H),8.05 (s, 1H), 7.85 (d, J = 1.0 Hz, 1H), 7.00 (s, 1H), 6.97 (dd, J = 2.0,7.2 Hz, 1H), 5.08-4.81 (m, 1H), 4.00 (s, 3H), 2.19-2.11 (m, 1H),1.75-1.60 (m, 1H), 1.21-1.13 (m, 1H); LCMS(electrospray) m/z 446.0 (M +H+). J methyl 5-chloro-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)pyrazolo[1,5-a]pyridin-5-yl)- 1H-indazole-7-carboxylate 555

¹H NMR (400 MHz, DMSO-d₆) δ 13.49 (br s, 1H), 11.18 (s, 1H), 8.66 (d, J= 7.0 Hz, 1H), 7.89 (s, 1H), 7.77 (s, 1H), 7.04-6.89 (m, 2H), 5.15-4.82(m, 1H), 4.58 (d, J = 4.3 Hz, 1H), 4.08 (br d, J = 5.4 Hz, 1H), 3.70 (brs, 1H), 2.90 (s, 3H), 2.11 (dt, J = 7.0, 13.6 Hz, 2H), 1.81-1.62 (m,5H), 1.59-1.43 (m, 2H), 1.25-1.13 (m, 1H); LCMS(electrospray) m/z 501.2(M + H+). J (1S,2S)-N-(5-(5-chloro-6-fluoro-7-((3-hydroxycyclopentyl)(methyl)amino)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 556

¹H NMR (400 MHz, DMSO-d₆) δ 13.88-13.56 (m, 1H), 11.20 (s, 1H), 8.70 (d,J = 7.1 Hz, 1H), 8.00 (s, 1H), 7.82 (d, J = 0.7 Hz, 1H), 6.99 (s, 1H),6.96 (d, J = 2.0 Hz, 1H), 5.05-4.85 (m, 1H), 3.13 (s, 3H), 2.93 (s, 3H),2.18-2.11 (m, 1H), 1.72- 1.62 (m, 1H), 1.18 (ddd, J = 2.9, 6.1, 12.3 Hz,1H); LCMS(electrospray) m/z459.1(M + H+). J5-chloro-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)pyrazolo[1,5-a]pyridin-5-yl)-N,N-dimethyl-1H-indazole-7-carboxamide 557

¹H NMR (400 MHz, DMSO-d₆) δ 13.18 (br d, J = 2.5 Hz, 1H), 11.14 (s, 1H),8.62 (d, J = 7.2 Hz, 1H), 7.74 (s, 1H), 7.62 (s, 1H), 6.90 (s, 1H),6.87-6.81 (m, 1H), 5.17-4.73 (m, 2H), 3.65-3.57 (m, 2H), 3.28-3.18 (m,2H), 2.97 (d, J = 2.3 Hz, 3H), 2.25- 2.10 (m, 4H), 1.76-1.58 (m, 1H),1.26-1.11 (m, 1H); LCMS(electrospray) m/z 441.1 (M + H+). J(1S,2S)-2-fluoro-N-(5-(6-fluoro-7-((2-hydroxyethyl)(methyl)amino)-5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide558

¹H NMR (400 MHz, DMSO-d₆) δ 13.43 (br s, 1H), 11.14 (s, 1H), 8.59 (d, J= 7.0 Hz, 1H), 7.78 (s, 1H), 7.62 (s, 1H), 6.91 (s, 1H), 6.87 (dd, J =1.9, 7.1 Hz, 1H), 5.06-4.82 (m, 1H), 2.97 (d, J = 2.0 Hz, 6H), 2.26 (s,3H), 2.19-2.10 (m, 1H), 1.73-1.61 (m, 1H), 1.22-1.12 (m, 1H);LCMS(electrospray) m/z 443 (M + H+). J(1S,2S)-N-(5-(7-(dimethylamino)-6- fluoro-5-(methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 559

¹H NMR (400 MHz, DMSO-d₆) δ 13.29 (br s, 1H), 11.15 (s, 1H), 8.62 (d, J= 7.0 Hz, 1H), 7.86 (br s, 1H), 7.71 (s, 1H), 7.00-6.86 (m, 2H), 5.44(br s, 1H), 5.11-4.94 (m, 1H), 4.90-4.77 (m, 1H), 4.40- 4.11 (m, 2H),2.25-2.09 (m, 2H), 2.04-1.86 (m, 1H), 1.84-1.57 (m, 5H), 1.30-1.08 (m,1H); LCMS(electrospray) m/z 487.2 (M + H+). J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-((3-hydroxycyclopentyl)amino)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 560

¹H NMR (400 MHz, DMSO-d₆) δ 13.68-13.53 (m, 1H), 11.24-11.17 (m, 1H),8.70 (d, J = 7.1 Hz, 1H), 8.67-8.60 (m, 1H), 7.99-7.93 (m, 1H), 7.81 (d,J = 0.9 Hz, 1H), 6.99 (s, 1H), 6.97-6.92 (m, 1H), 5.07-4.81 (m, 1H),2.91 (d, J = 4.4 Hz, 3H), 2.20-2.10 (m, 1H), 1.75-1.55 (m, 1H), 1.07 (s,1H); LCMS(electrospray) m/z 445.1(M + H+). J5-chloro-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)pyrazolo[1,5-a]pyridin-5-yl)-N-methyl-1H-indazole-7-carboxamide 561

¹H NMR (400 MHz, DMSO-d₆) δ 11.18 (br s, 1H), 8.65 (d, J = 7.2 Hz, 1H),7.88 (s, 1H), 7.76 (s, 1H), 7.09-6.87 (m, 2H), 5.08-4.84 (m, 1H),3.87-3.71 (m, 1H), 3.59-3.43 (m, 1H), 3.60-3.42 (m, 1H), 2.89-2.81 (m,3H), 2.46-2.39 (m, 2H), 2.21-2.09 (m, 1H), 2.24-2.07 (m, 1H), 2.20-1.95(m, 1H), 1.99 (br d, J = 4.9 Hz, 1H), 1.79-1.62 (m, 3H), 1.26-1.12 (m,2H); LCMS(electrospray) m/z 487.2 (M + H+). J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-((3-hydroxycyclobutyl)(methyl)amino)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 562

¹H NMR (400 MHz, DMSO-d₆) δ 13.47 (br s, 1H), 11.11 (s, 1H), 8.64 (d, J= 7.1 Hz, 1H), 7.83 (s, 1H), 7.65 (s, 1H), 6.91 (s, 1H), 6.86 (dd, J =1.9, 7.1 Hz, 1H), 2.24 (d, J = 2.9 Hz, 3H), 2.00-1.87 (m, 1H), 0.88-0.77(m, 4H); LCMS(electrospray) m/z 395.12 (M + H+). JN-(5-(6-fluoro-5-methyl-7-(methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropanecarboxamide 563

¹H NMR (400 MHz, METHANOL-d₄) δ 8.55- 8.47 (m, 1H), 7.79-7.72 (m, 1H),7.58-7.54 (m, 1H), 7.00-6.93 (m, 1H), 6.89-6.83 (m, 1H), 5.02- 4.93 (m,1H), 4.60-4.56 (m, 1H), 3.29-3.24 (m, 2H), 3.01-2.94 (m, 3H), 2.33-2.25(m, 3H), 2.17- 2.07 (m, 1H), 1.89-1.77 (m, 1H), 1.27-1.19 (m, 1H),1.15-1.09 (m, 3H); LCMS(electrospray) m/z 425.2 (M + H+). J(1S,2S)-N-(5-(7-(ethyl(methyl)amino)-6- fluoro-5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 564

¹H NMR (400 MHz, METHANOL-d₄) δ 8.43- 8.38 (m, 1H), 7.77-7.72 (m, 1H),7.59-7.54 (m, 1H), 6.89-6.86 (m, 1H), 6.85-6.81 (m, 1H), 4.88- 4.82 (m,1H), 4.72-4.64 (m, 1H), 3.20-3.15 (m, 2H), 3.20 (br s, 1H), 2.90 (d, J =1.8 Hz, 2H), 2.95- 2.88 (m, 1H), 2.04-1.94 (m, 1H), 1.78-1.65 (m, 1H),1.17-1.07 (m, 1H), 1.05-0.99 (m, 3H); LCMS(electrospray) m/z 445.2 (M +H+). J (1S,2S)-N-(5-(5-chloro-7- (ethyl(methyl)amino)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 565

¹H NMR (400 MHz, DMSO-d₆) δ 11.18 (s, 1H), 8.62 (d, J = 7.1 Hz, 1H),7.80 (d, J = 4.8 Hz, 1H), 7.62 (d, J = 0.9 Hz, 1H), 6.92 (s, 1H), 6.80(dd, J = 1.9, 7.1 Hz, 1H), 5.08-4.70 (m, 1H), 3.02 (d, J = 2.3 Hz, 6H),2.20-2.12 (m, 1H), 1.73-1.62 (m, 1H), 1.22-1.14 (m, 1H);LCMS(electrospray) m/z 465.1 (M + H+). J(1S,2S)-N-(5-(7-(dimethylamino)-6-fluoro-5-(trifluoromethyl)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 566

¹H NMR (400 MHz, DMSO-d₆) δ 13.44 (br s, 1H), 11.19 (s, 1H), 8.68 (d, J= 7.1 Hz, 1H), 7.86 (s, 1H), 7.73 (s, 1H), 6.97 (s, 1H), 6.89 (dd, J =1.9, 7.2 Hz, 1H), 5.07-4.80 (m, 1H), 2.74 (d, J = 6.4 Hz, 3H), 2.28 (d,J = 3.2 Hz, 3H), 2.20-2.09 (m, 1H), 1.74- 1.61 (m, 1H), 1.25-1.13 (m,1H); LCMS(electrospray) m/z 409.14 (M + H+). J(1S,2S)-N-(5-(7-acetyl-6-fluoro-5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 567

¹H NMR (400 MHz, DMSO-d₆) δ 13.47 (br s, 1H), 11.28 (s, 1H), 8.65 (d, J= 7.1 Hz, 1H), 7.83 (s, 1H), 7.67 (s, 1H), 6.89 (s, 1H), 6.87 (d, J =1.8 Hz, 1H), 5.03-4.81 (m, 1H), 2.23 (d, J = 2.8 Hz, 3H), 1.64- 1.45 (m,1H), 1.27 (qd, J = 6.5, 13.1 Hz, 1H); LCMS(electrospray) m/z 413.11 (M +H+). J (1S,2R)-2-fluoro-N-(5-(6-fluoro-5-methyl-7-(methylthio)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropane-1-carboxamide 568

¹H NMR (400 MHz, DMSO-d₆) δ 13.47 (br s, 1H), 11.28 (s, 1H), 8.65 (d, J= 7.1 Hz, 1H), 7.83 (s, 1H), 7.67 (d, J = 0.7 Hz, 1H), 6.88 (s, 1H),6.87 (d, J = 1.8 Hz, 1H), 5.04-4.79 (m, 1H), 2.49-2.40 (m, 3H), 2.23 (d,J = 2.8 Hz, 3H), 1.62-1.45 (m, 1H), 1.27 (qd, J = 6.4, 13.1 Hz, 1H);LCMS(electrospray) m/z 413.11 (M + H+). J(1R,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl- 7-(methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide 569

¹H NMR (400 MHz, DMSO-d₆) δ 13.45 (br s, 1H), 11.10 (s, 1H), 8.61 (d, J= 7.1 Hz, 1H), 7.81 (s, 1H), 7.66 (s, 1H), 7.52 (d, J = 9.3 Hz, 1H),6.91 (s, 1H), 6.88 (dd, J = 1.8, 7.1 Hz, 1H), 2.26 (s, 3H), 2.00- 1.88(m, 1H), 0.90-0.77 (m, 4H); LCMS(electrospray) m/z 382.1(M + H+) JN-(5-(6-fluoro-5-(methylthio)-1H-indazol- 4-yl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide 570

¹H NMR (400 MHz, DMSO-d₆) δ 13.43 (br s, 1H), 11.17 (s, 1H), 8.66 (d, J= 7.1 Hz, 1H), 7.84 (s, 1H), 7.73-7.67 (m, 1H), 6.94 (s, 1H), 6.89 (dd,J = 2.0, 7.1 Hz, 1H), 5.16-4.74 (m, 1H), 3.12 (s, 3H), 2.92 (s, 3H),2.24 (d, J = 2.9 Hz, 3H), 2.19-2.10 (m, 1H), 1.74-1.60 (m, 1H), 1.18(tdd, J = 6.2, 9.1, 12.3 Hz, 1H); LCMS(electrospray) m/z 439.2 (M + H+).J 6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)pyrazolo[1,5-a]pyridin-5-yl)- N,N,5-trimethyl-1H-indazole-7-carboxamide 571

¹H NMR (400 MHz, DMSO-d₆) δ 13.42 (br s, 1H), 11.28 (br s, 1H), 8.63 (d,J = 7.1 Hz, 1H), 7.81 (s, 1H), 7.67 (s, 1H), 7.52 (d, J = 9.3 Hz, 1H),6.93- 6.87 (m, 2H), 5.05-4.81 (m, 1H), 2.48-2.42 (m, 1H), 2.26 (s, 3H),1.61-1.46 (m, 1H), 1.33-1.20 (m, 1H); LCMS(electrospray) m/z 400.1(M +H+). J (1R,2S)-2-fluoro-N-(5-(6-fluoro-5- (methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide 572

¹H NMR (400 MHz, DMSO-d₆) δ 13.40 (br s, 1H), 11.28 (s, 1H), 8.63 (d, J= 7.0 Hz, 1H), 7.81 (s, 1H), 7.67 (s, 1H), 7.52 (d, J = 9.2 Hz, 1H),6.93-6.87 (m, 2H), 5.03-4.80 (m, 1H), 2.46-2.42 (m, 1H), 2.26 (s, 3H),1.61-1.46 (m, 1H), 1.27 (qd, J = 6.3, 13.0 Hz, 1H); LCMS(electrospray)m/z 400.1(M + H+). J (1S,2R)-2-fluoro-N-(5-(6-fluoro-5-(methylthio)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropane-1-carboxamide 573

¹H NMR (400 MHz, DMSO-d₆) δ 13.42 (br s, 1H), 11.15 (s, 1H), 8.62 (d, J= 7.0 Hz, 1H), 7.82 (s, 1H), 7.68 (s, 1H), 7.52 (d, J = 9.4 Hz, 1H),6.93 (s, 1H), 6.90 (dd, J = 1.8, 7.1 Hz, 1H), 5.06-4.83 (m, 1H), 2.26(s, 3H), 2.15 (td, J = 7.1, 14.1 Hz, 1H), 1.74- 1.61 (m, 1H), 1.22-1.12(m, 1H); LCMS(electrospray) m/z 400.1(M + H+). J(1R,2R)-2-fluoro-N-(5-(6-fluoro-5- (methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide 574

¹H NMR (400 MHz, DMSO-d₆) δ 13.47 (br s, 1H), 11.16 (s, 1H), 8.65 (d, J= 7.1 Hz, 1H), 7.84 (s, 1H), 7.67 (s, 1H), 6.93 (s, 1H), 6.87 (dd, J =1.8, 7.1 Hz, 1H), 5.08-4.79 (m, 1H), 3.30 (s, 3H), 2.25-2.23 (m, 1H),2.24 (d, J = 2.9 Hz, 3H), 2.14 (br dd, J = 6.0, 8.1 Hz, 1H), 1.76-1.60(m, 1H), 1.24-1.13 (m, 1H); LCMS(electrospray) m/z 413.11 (M + H+). J(1R,2R)-2-fluoro-N-(5-(6-fluoro-5-methyl- 7-(methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide 575

¹H NMR (400 MHz, DMSO-d₆) δ 13.74 (s, 1H), 11.22 (s, 1H), 8.72 (d, J =7.1 Hz, 1H), 8.40 (s, 1H), 8.02 (s, 1H), 7.85 (d, J = 1.0 Hz, 1H), 7.02(s, 1H), 6.97 (dd, J = 1.9, 7.2 Hz, 1H), 5.14-4.76 (m, 1H), 2.77 (d, J =6.1 Hz, 3H), 2.21-2.12 (m, 1H), 1.75- 1.61 (m, 1H), 1.26-1.12 (m, 2H);LCMS(electrospray) m/z 430.3 (M + H+). J(1S,2S)-N-(5-(7-acetyl-5-chloro-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 576

¹H NMR (400 MHz, DMSO-d₆) δ 13.70-13.43 (m, 1H), 11.22 (s, 1H), 8.71 (d,J = 6.8 Hz, 1H), 8.08 (s, 2H), 7.95 (s, 1H), 7.82 (s, 1H), 7.03-6.91 (m,2H), 5.10-4.81 (m, 1H), 2.15 (d, J = 6.8 Hz, 1H), 1.76-1.59 (m, 1H),1.18 (d, J = 7.2 Hz, 1H); LCMS(electrospray) m/z 431.1 (M + H+). J5-chloro-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)pyrazolo[1,5-a]pyridin-5-yl)- 1H-indazole-7-carboxamide 577

¹H NMR (400 MHz, DMSO-d₆) δ 13.38 (br s, 1H), 11.14 (s, 1H), 8.60 (d, J= 6.9 Hz, 1H), 7.78 (s, 1H), 7.64 (s, 1H), 6.91 (s, 1H), 6.88 (dd, J =1.6, 7.1 Hz, 1H), 5.06-4.83 (m, 1H), 3.23 (q, J = 6.7 Hz, 2H), 2.95 (s,3H), 2.26 (s, 3H), 2.19-2.10 (m, 1H), 1.74- 1.61 (m, 1H), 1.21-1.14 (m,1H), 1.07 (t, J = 7.0 Hz, 3H); LCMS(electrospray) m/z 457 (M + H+). J(1S,2S)-N-(5-(7-(ethyl(methyl)amino)-6-fluoro-5-(methylthio)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 578

¹H NMR (400 MHz, DMSO-d₆) δ 13.62-12.96 (m, 1H), 11.16 (br s, 1H), 8.64(d, J = 7.1 Hz, 1H), 7.98 (s, 1H), 7.83 (s, 1H), 7.50 (d, J = 10.4 Hz,1H), 7.04 (dd, J = 1.8, 7.1 Hz, 1H), 6.95 (s, 1H), 5.06- 4.81 (m, 1H),3.86 (q, J = 6.9 Hz, 2H), 2.15 (td, J = 7.0, 13.6 Hz, 1H), 1.73-1.62 (m,1H), 1.22- 1.15 (m, 1H), 1.11 (t, J = 7.0 Hz, 3H). LCMS: m/z 398.0 (M +H+) J (1S,2S)-N-(5-(5-ethoxy-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 579

¹H NMR (400 MHz, DMSO-d₆) δ 11.31-11.12 (m, 1H), 8.82-8.55 (m, 1H),8.00-7.87 (m, 1H), 7.85- 7.70 (m, 1H), 7.03-6.90 (m, 2H), 5.10-4.82 (m,1H), 2.56-2.53 (m, 3H), 2.24-2.11 (m, 1H), 1.75- 1.61 (m, 1H), 1.26-1.13(m, 1H); LCMS(electrospray) m/z 402.1 (M + H+). J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 580

¹H NMR (400 MHz, DMSO-d₆) δ 13.31-12.98 (m, 1H), 11.21-11.07 (m, 1H),8.61 (d, J = 7.0 Hz, 1H), 7.78-7.71 (m, 1H), 7.64-7.58 (m, 1H), 6.93-6.88 (m, 2H), 6.84 (br d, J = 7.1 Hz, 1H), 5.06- 4.82 (m, 1H), 4.07 (brt, J = 5.9 Hz, 2H), 3.35- 3.27 (m, 2H), 2.98 (s, 3H), 2.53 (d, J = 4.5Hz, 3H), 2.20 (d, J = 3.0 Hz, 3H), 2.16-2.09 (m, 1H), 1.72- 1.61 (m,1H), 1.20-1.13 (m, 1H); LCMS(electrospray) m/z = 498.2 (M + H+). J2-((6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)pyrazolo[1,5-a]pyridin-5-yl)- 5-methyl-1H-indazol-7-yl)(methyl)amino)ethyl methylcarbamate 581

¹H NMR (400 MHz, DMSO-d₆) δ 1.12-1.24 (m, 1 H), 1.61-1.74 (m, 1 H),2.11-2.20 (m, 1 H), 4.82- 5.07 (m, 1 H), 6.95-6.98 (m, 1 H), 6.99 (s, 1H) 7.50 (s, 1 H), 7.63 (s, 1 H), 7.77 (s, 1 H), 7.83 (d, J = 1.00 Hz, 1H), 8.06 (s, 1 H), 8.71 (d, J = 7.13 Hz, 1 H), 11.20 (s, 1 H),13.85-13.92 (m, 1 H); LCMS(electrospray) m/z 438.1 (M + H+). J(1S,2S)-N-(5-(5-chloro-7- (difluoromethyl)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 582

¹H NMR (400 MHz, DMSO-d₆) δ 11.19 (s, 1H), 8.69 (d, J = 7.1 Hz, 1H),8.06 (s, 1H), 7.74 (s, 1H), 6.97 (s, 1H), 6.90 (dd, J = 1.8, 7.1 Hz,1H), 5.10- 4.72 (m, 1H), 2.26 (d, J = 2.6 Hz, 3H), 2.15 (td, J = 6.6,13.5 Hz, 1H), 1.73-1.60 (m, 1H), 1.25- 1.13 (m, 1H); LCMS(electrospray)m/z 393.1 (M + H+). J (1S,2S)-N-(5-(7-cyano-6-fluoro-5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 583

¹H NMR (400 MHz, DMSO-d₆) δ 13.38 (s, 1H), 11.15 (s, 1H), 8.61 (d, J =7.2 Hz, 1H), 8.29 (s, 1H), 7.93 (d, J = 1.0 Hz, 1H), 7.23 (d, J = 13.7Hz, 1H), 7.16 (dd, J = 2.0, 7.2 Hz, 1H), 6.94 (s, 1H), 5.06- 4.83 (m,1H), 2.95 (d, J = 2.0 Hz, 6H), 2.14 (br s, 1H), 1.77-1.57 (m, 1H), 1.17(br s, 1H); LCMS(electrospray) m/z 397.2 (M + H+). J(1S,2S)-N-(5-(7-(dimethylamino)-6- fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 584

¹H NMR (400 MHz, DMSO-d₆) δ 13.31-13.17 (m, 1H), 11.26-11.08 (m, 1H),8.66 (d, J = 7.1 Hz, 1H), 8.49-8.38 (m, 1H), 7.85-7.76 (m, 1H), 7.70 (s,1H), 6.95 (s, 1H), 6.88 (s, 1H), 5.07-4.82 (m, 1H), 2.90 (d, J = 4.6 Hz,3H), 2.25 (d, J = 3.1 Hz, 3H), 2.15 (td, J = 6.7, 13.8 Hz, 1H),1.74-1.62 (m, 1H), 1.21-1.09 (m, 1H); LCMS(electrospray) m/z 425.1 (M +H+). J 6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)pyrazolo[1,5-a]pyridin-5-yl)-N,5-dimethyl-1H-indazole-7-carboxamide 585

¹H NMR (400 MHz, DMSO-d₆) δ 13.82-13.52 (m, 1H), 11.19 (s, 1H), 8.69 (d,J = 7.0 Hz, 1H), 7.91 (s, 1H), 7.70 (d, J = 0.9 Hz, 1H), 6.96 (s, 1H),6.86 (dd, J = 1.9, 7.1 Hz, 1H), 5.06-4.83 (m, 1H), 2.68-2.63 (m, 2H),2.19-2.10 (m, 1H), 1.74-1.62 (m, 1H), 1.20-1.14 (m, 1H), 1.10 (t, J =7.5 Hz, 3H); LCMS(electrospray) m/z 450.2 (M + H+). J(1S,2S)-N-(5-(5-ethyl-6-fluoro-7- (trifluoromethyl)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 586

¹H NMR (400 MHz, DMSO-d₆) δ 11.21 (s, 1H), 8.73 (d, J = 7.2 Hz, 1H),8.24 (s, 1H), 7.86 (s, 1H), 7.02 (s, 1H), 6.97 (dd, J = 1.9, 7.2 Hz,1H), 5.10- 4.78 (m, 1H), 2.22-2.10 (m, 1H), 1.76-1.58 (m, 1H), 1.22-1.15(m, 1H); LCMS(electrospray) m/z 413.2 (M + H+). J(1S,2S)-N-(5-(5-chloro-7-cyano-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 587

¹H NMR (400 MHz, DMSO-d₆) δ 14.11 (s, 1H), 11.17 (s, 1H), 8.68-8.66 (m,1H), 8.45(s, 1H), 8.04 (s, 1H), 7.52 (d, J = 11.2 Hz, 1H), 7.22-7.21 (m,1H), 6.99 (s, 1H), 5.02-4.86 (m, 1H), 2.15 (br s, 1H), 1.72-1.70 (m, 1H) 1.19-1.18 (m, 1 H); LCMS(electrospray) m/z 438.2 (M + H+). J(1S,2S)-2-fluoro-N-(5-(6-fluoro-7- (trifluoromethoxy)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide 588

¹H NMR (400 MHz, DMSO-d₆) δ 13.84-13.52 (m, 1H), 11.32-11.10 (m, 1H),8.75-8.60 (m, 1H), 7.97-7.76 (m, 1H), 7.72-7.64 (m, 1H), 6.99-6.91 (m,1H), 6.89-6.80 (m, 1H), 5.09-4.81 (m, 1H), 4.26-4.07 (m, 2H), 2.75-2.62(m, 2H), 2.24-2.10 (m, 1H), 1.77-1.62 (m, 1H), 1.23-1.15 (m, 1H),1.15-1.09 (m, 3H); LCMS(electrospray) m/z 453.1 (M + H+). J(1S,2S)-N-(5-(7-((cyanomethyl)thio)-5- ethyl-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 589

¹H NMR (400 MHz, DMSO-d₆) δ 13.64 (s, 1 H) 11.17 (s, 1 H) 8.65 (d, J =7.2 Hz, 1 H) 8.38 (s, 1 H) 8.02 (s, 1 H) 7.37 (d, J = 8.8 Hz, 1 H)7.22-7.19 (m, 1 H) 6.98 (s, 1 H), 5.05-4.84 (m, 1 H) 2.52 (s, 3 H)2.16-2.13 (m, 1H) 1.72-1.64 (m, 1H) 1.20- 1.15 (m, 1 H);LCMS(electrospray) m/z 400.1 (M + H+). J(1S,2S)-2-fluoro-N-(5-(6-fluoro-7- (methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide 590

¹H NMR (400 MHz, DMSO-d₆) δ 13.74 (br s, 1H), 8.24 (d, J = 8.3 Hz, 1H),7.79 (s, 1H), 7.76 (d, J = 11.9 Hz, 1H), 7.66 (d, J = 8.3 Hz, 1H),5.19-4.94 (m, 1H), 2.26 (td, J = 6.9, 13.6 Hz, 1H), 1.84-1.70 (m, 1H),1.39-1.27 (m, 1H); LCMS(electrospray) m/z 440.2 (M + H+). J(1S,2S)-2-fluoro-N-(5-(6-fluoro-5- (trifluoromethyl)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide 591

¹H NMR (400 MHz, DMSO-d₆) δ 13.55 (s, 1H), 11.18 (s, 1H), 8.67 (d, J =7.1 Hz, 1H), 7.89 (d, J = 0.7 Hz, 1H), 7.72-7.41 (m, 2H), 6.95 (s, 1H),6.89 (dd, J = 1.8, 7.0 Hz, 1H), 5.09-4.81 (m, 1H), 2.24 (d, J = 2.6 Hz,3H), 2.19-2.11 (m, 1H), 1.76-1.60 (m, 1H), 1.25-1.11 (m, 1H);LCMS(electrospray) m/z 418.1 (M + H+). J(1S,2S)-N-(5-(7-(difluoromethyl)-6- fluoro-5-methyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 592

¹H NMR (400 MHz, DMSO-d₆) δ 13.95 (s, 1H), 11.18 (s, 1H), 8.67 (d, J =7.1 Hz, 1H), 7.94 (s, 1H), 7.72 (s, 1H), 6.95 (s, 1H), 6.90 (dd, J =1.8, 7.1 Hz, 1H), 5.11-4.78 (m, 1H), 2.28 (d, J = 2.8 Hz, 3H), 2.20-2.10(m, 1H), 1.74-1.61 (m, 1H), 1.24-1.12 (m, 1H); LCMS(electrospray) m/z452.2 (M + H+). J (1S,2S)-2-fluoro-N-(5-(6-fluoro-5-methyl-7-(trifluoromethoxy)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropane-1-carboxamide 593

¹H NMR (400 MHz, DMSO-d₆) δ 13.43-13.58 (m, 1 H) 11.13 (s, 1 H) 8.62 (d,J = 7.13 Hz, 1 H) 8.36 (s, 1 H) 7.94 (d, J = 1.25 Hz, 1 H) 7.36 (s, 2 H)7.17 (dd, J = 7.25, 2.00 Hz, 1 H) 6.95 (s, 1 H) 4.80- 5.07 (m, 1 H) 2.63(s, 3 H) 2.10-2.18 (m, 1 H) 1.62-1.73 (m, 1 H) 1.17 (ddt, J = 12.32,9.04, 6.27, 6.27 Hz, 1 H); LCMS(electrospray) m/z = 382.1 (M + H+). J(1S,2S)-2-fluoro-N-(5-(7-(methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)cyclopropane-1-carboxamide 594

¹H NMR (400 MHz, DMSO-d₆) δ 13.69 (s, 1H), 11.14 (s, 1H), 8.93 (s, 1H),8.26-8.23 (m, 2H), 7.65 (d, J = 9.3 Hz, 1H), 7.51-7.39 (m, 1H),5.11-4.77 (m, 1H), 4.13 (s, 3H), 2.18 (td, J = 6.8, 13.8 Hz, 1H),1.81-1.59 (m, 1H), 1.27-1.11 (m, 1H); LCMS(electrospray) m/z 470.2 (M +H+). J (1S,2S)-N-(5-(5-chloro-6-fluoro-7-(1-methyl-1H-tetrazol-5-yl)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 595

¹H NMR (400 MHz, DMSO-d₆) δ 13.26 (br s, 1H), 11.11 (s, 1H), 8.57 (br d,J = 7.1 Hz, 1H), 8.28 (s, 1H), 7.84 (s, 1H), 7.26 (br d, J = 7.7 Hz,1H), 7.13 (dd, J = 2.0, 7.3 Hz, 1H), 6.90 (s, 1H), 6.80 (br d, J = 7.7Hz, 1H), 5.08-4.79 (m, 1H), 2.93 (s, 6H), 2.14 (quin, J = 6.9 Hz, 1H),1.74-1.60 (m, 1H), 1.17 (tdd, J = 6.2, 9.0, 12.3 Hz, 1H);LCMS(electrospray) m/z 379.1 (M + H+). J(1S,2S)-N-(5-(7-(dimethylamino)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 596

¹H NMR (400 MHz, DMSO-d₆) δ 13.63 (s, 1H), 11.19 (s, 1H), 8.63 (d, J =7.2 Hz, 1H), 8.45 (br, 1H), 7.97 (s, 1H), 7.84 (s, 1H), 6.99 (s, 1H),6.85 (d, J = 7.2 Hz, 1H), 5.04-4.85 (m, 1H), 3.53 (s, 3H), 2.16-2.12 (m,1H), 1.70-1.63 (m, 1H), 1.28- 1.12 (m, 1H); LCMS (electrospray) m/z495.1 (M + H)+. J (1S,2S)-N-(5-(5-chloro-6-fluoro-7-(methyl(pyrimidin-2-yl)amino)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 597

¹H NMR (400 MHz, DMSO-d₆) δ 13.67 (s, 1H), 11.19 (s, 1H), 8.67 (d, J =7.2 Hz, 1H), 7.82 (s, 1H), 7.69 (s, 1H), 6.94 (s, 1H), 6.85 (d, J = 7.2Hz, 1H), 5.04-4.87 (m, 1H), 4.50 (q, J = 7.2 Hz, 1H), 2.69- 2.60 (m,2H), 4.23 (s, 2H), 2.16-2.12 (m, 1H), 1.70-1.63 (m, 1H), 1.60 (d, J = 12Hz, 3H), 1.28- 1.11 (m, 4H); LCMS (electrospray) m/z 467.1 (M + H)+. J(1S,2S)-N-(5-(5-chloro-7- ((cyanomethyl)thio)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide598

¹H NMR (400 MHz, DMSO-d₆) δ 14.15 (s, 1H), 11.17 (s, 1H), 8.63 (d, J =7.6 Hz, 1H), 7.96 (s, 1H), 7.67 (s, 1H), 6.94 (s, 1H), 6.88 (d, J = 7.2Hz, 1H), 5.04-4.87 (m, 1H), 2.30 (s, 3H), 2.15-2.13 (m, 1H), 1.71-1.64(m, 1H), 1.24-1.18 (m, 1H); LCMS (electrospray) m/z 418.10 (M + H)+. J(1R,2R)-N-(5-(6,7-difluoro-5- (methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 599

¹H NMR (400 MHz, DMSO-d₆) δ 14.13 (s, 1H), 11.29 (s, 1H), 8.64 (d, J =6.0 Hz, 1H), 7.96 (s, 1H), 7.66 (s, 1H), 6.90-6.88 (m, 2H), 5.00-4.84(m, 1H), 2.50-2.43 (m, 1H), 2.30 (s, 3H), 1.58-1.49 (m, 1H), 1.30-1.24(m, 1H); LCMS (electrospray) m/z 418.10 (M + H)+. J(1S,2R)-N-(5-(6,7-difluoro-5- (methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 600

¹H NMR (400 MHz, DMSO-d₆) δ 14.11 (s, 1H), 11.29 (s, 1H), 8.64 (d, J =7.2 Hz, 1H), 7.96 (s, 1H), 7.66 (s, 1H), 6.90-6.88 (m, 2H), 5.00-4.84(m, 1H), 2.50- 2.43 (m, 1H), 2.30 (s, 3H), 1.57 (m, 1H), 1.29-1.24 (m,1H); LCMS (electrospray) m/z 418.10 (M + H)+. J(1R,2S)-N-(5-(6,7-difluoro-5- (methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 601

¹H NMR (400 MHz, DMSO-d₆) δ 13.39 (s, 1H), 11.19 (s, 1H), 9.49 (s, 1H),8.69 (d, J = 7.2 Hz, 1 H), 8.42 (d, J = 4.4 Hz, 1H), 7.91 (s, 1H), 7.83-7.82 (m, 1H), 6.99-6.97 (m, 1H), 6.86 (t, J = 5.0 Hz, 1H), 5.05-4.85 (m,1H), 2.17-2.13 (m, 1H), 1.71-1.63 (m, 1H), 1.21-1.15 (m, 1H); LCMS(electrospray) m/z 481.10 (M + H)+. J (1S,2S)-N-(5-(5-chloro-6-fluoro-7-(pyrimidin-2-ylamino)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 602

¹H NMR (400 MHz, DMSO-d₆) δ 13.63 (s, 1H), 11.21 (s, 1H), 8.71 (d, J =7.2 Hz, 1H), 8.05 (s, 1H), 7.85 (s, 1H), 7.00 (s, 1H), 6.98 (d, J = 7.2Hz, 1H), 5.04-4.87 (m, 1H), 4.23 (s, 2H), 2.16-2.12 (m, 1H), 1.70-1.63(m, 1H), 1.28-1.12 (m, 1H); LCMS (electrospray) m/z 459.1 (M + H)+. J(1S,2S)-N-(5-(7-((1-cyanoethyl)thio)-5- ethyl-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 603

¹H NMR (400 MHz, DMSO-d₆) δ 13.65 (s, 1H), 11.19 (s, 1H), 8.67 (d, J =7.2 Hz, 1H), 7.81 (s, 1H), 7.71 (s, 1H), 6.94 (s, 1H), 6.87 (d, J = 7.2Hz, 1H), 5.04-4.84 (m, 1H), 2.66-2.63 (m, 2H), 2.18- 2.11 (m, 1H), 1.73(s, 6H), 1.70-1.62 (m, 1H), 1.28-1.12 (m, 1H), 1.12 (t, J = 5.2 Hz, 3H);LCMS (electrospray) m/z 481.1 (M + H)+. J(1S,2S)-N-(5-(7-((2-cyanopropan-2-yl)thio)-5-ethyl-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 604

¹H NMR (400 MHz, DMSO-d₆) δ 13.93-13.02 (m, 1H), 11.17 (s, 1H), 8.63 (d,J = 7.2 Hz, 1H), 8.05 (s, 1H), 7.69 (d, J = 1.0 Hz, 1H), 7.52 (dd, J =0.8, 9.5 Hz, 1H), 6.96 (s, 1H), 6.89 (td, J = 2.2, 7.2 Hz, 1H),5.14-4.72 (m, 1H), 2.85 (s, 3H), 2.72 (d, J = 1.6 Hz, 3H), 2.14 (td, J =6.9, 13.8 Hz, 1H), 1.75-1.59 (m, 1H), 1.17 (tdd, J = 6.2, 9.1, 12.3 Hz,1H); LCMS(electrospray) m/z 425.2 (M + H+). J 6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1- carboxamido)pyrazolo[1,5-a]pyridin-5-yl)-N,N-dimethyl-1H-indazole-7-carboxamide 605

¹H NMR (400 MHz, DMSO-d₆) δ 13.93-13.02 (m, 1H), 11.17 (s, 1H), 8.63 (d,J = 7.2 Hz, 1H), 8.05 (s, 1H), 7.69 (d, J = 1.0 Hz, 1H), 7.52 (dd, J =0.8, 9.5 Hz, 1H), 6.96 (s, 1H), 6.89 (td, J = 2.2, 7.2 Hz, 1H),5.14-4.72 (m, 1H), 2.85 (s, 3H), 2.72 (d, J = 1.6 Hz, 3H), 2.14 (td, J =6.9, 13.8 Hz, 1H), 1.75-1.59 (m, 1H), 1.17 (tdd, J = 6.2, 9.1, 12.3 Hz,1H); LCMS(electrospray) m/z 425.2 (M + H+ J 6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1- carboxamido)pyrazolo[1,5-a]pyridin-5-yl)-N,N-dimethyl-1H-indazole-5-carboxamide 606

¹H NMR (400 MHz, DMSO-d₆) δ 11.16 (s, 1H), 8.64 (br d, J = 7.1 Hz, 1H),8.06 (s, 1H), 7.83 (s, 1H), 7.03 (br dd, J = 1.8, 7.1 Hz, 1H), 6.96 (s,1H), 5.06-4.82 (m, 1H), 3.86 (br d, J = 7.0 Hz, 2H), 2.55 (s, 3H),2.18-2.12 (m, 1H), 1.73-1.61 (m, 1H), 1.26-1.15 (m, 1H), 1.11 (br t, J =6.9 Hz, 3H); LCMS(electrospray) m/z 444.2 (M + H+). J(1S,2S)-N-(5-(5-ethoxy-6-fluoro-7- (methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 607

¹H NMR (400 MHz, DMSO-d₆) δ 14.06-13.49 (m, 1H), 10.62 (br s, 1H), 9.03(d, J = 7.0 Hz, 1H), 8.56 (s, 1H), 8.25 (s, 1H), 7.58 (s, 1H), 7.44 (dd,J = 1.8, 7.1 Hz, 1H), 5.46-5.25 (m, 1H), 2.69 (br s, 1H), 2.27- 2.21 (m,1H), 1.69-1.61 (m, 1H); LCMS(electrospray) m/z 472.0 (M + H+). J(1S,2S)-N-(5-(5-chloro-6-fluoro-7- (trifluoromethoxy)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 608

¹H NMR (400 MHz, DMSO-d₆) δ 13.64 (s, 1H), 11.19 (s, 1H), 8.67 (d, J =7.2 Hz, 1H), 7.82 (s, 1H), 7.71 (s, 1H), 6.94 (s, 1H), 6.88 (d, J = 7.2Hz, 1H), 5.04-4.84 (m, 1H), 2.66-2.63 (m, 2H), 2.18- 2.11 (m, 1H),1.73-7.72 (m, 2H), 1.70-1.62 (m, 1H), 1.62-1.60 (m, 1H), 1.28-1.12 (m,1H), 1.12 (t, J = 5.2 Hz, 3H); LCMS (electrospray) m/z 479.1 (M + H)+. J(1S,2S)-N-(5-(7-((1- cyanocyclopropyl)thio)-5-ethyl-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 609

¹H NMR (400 MHz, DMSO-d₆) δ 13.63 (s, 1H), 11.20 (s, 1H), 8.99 (s, 1H),8.69 (d, J = 7.2 Hz, 1H), 8.21 (d, J = 6.4 Hz, 2H), 7.99 (s, 1H),7.83-7.82 (m, 1H), 7.01-6.98 (m, 2H), 6.62 (d, J = 4.8 Hz, 2H),5.04-4.85 (m, 1H), 2.17-2.12 (m, 1H), 1.71- 1.63 (m, 1H), 1.21-1.16 (m,1H); LCMS (electrospray) m/z 480.10 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7- (pyridin-4-ylamino)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 610

¹H NMR (400 MHz, DMSO-d₆) δ 13.28 (br s, 1H), 11.15 (s, 1H), 8.60 (d, J= 7.0 Hz, 1H), 7.96 (s, 1H), 7.77 (s, 1H), 7.01 (dd, J = 1.8, 7.3 Hz,1H), 6.92 (s, 1H), 5.04-4.83 (m, 1H), 3.83 (q, J = 7.0 Hz, 2H), 2.98 (brs, 6H), 2.18-2.11 (m, 1H), 1.72-1.6 (m, 1H), 1.18 (br s, 1H), 1.11 (t, J= 7.0 Hz, 3H); LCMS(electrospray) m/z 441.1 (M + H+). J(1S,2S)-N-(5-(7-(dimethylamino)-5- ethoxy-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 611

¹H NMR (400 MHz, DMSO-d₆) δ 13.96 (s, 1H), 11.17 (s, 1H), 8.64 (d, J =7.2 Hz, 1H), 8.18-8.12 (m, 1H), 7.81 (s, 1H), 7.02-6.93 (m, 2H), 5.04-4.84 (m, 1H), 3.96-3.82 (m, 2H), 2.18-2.09 (m, 1H), 1.70-1.60 (m, 1H),1.20-1.16 (m, 1H), 1.12 (t, J = 6.8 Hz, 3H); LCMS(electrospray) m/z416.1 (M + H+). J (1S,2S)-N-(5-(5-ethoxy-6,7-difluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 612

¹H NMR (400 MHz, DMSO-d₆) δ 13.85 (s, 1H), 11.22 (s, 1H), 8.71 (d, J =7.2 Hz, 1H), 8.01 (s, 1H), 7.82 (s, 1H), 6.99 (s, 1H), 6.97 (s, J = 7.2Hz, 1H), 5.04-4.84 (m, 1H), 4.72 (s, 2H), 3.03 (s, 3H), 2.18-2.11 (m,1H), 1.70-1.62 (m, 1H), 1.28-1.12 (m, 1H); LCMS (electrospray) m/z 484.1(M + H)+. J 5-chloro-N-(cyanomethyl)-6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1-carboxamido)pyrazolo[1,5-a]pyridin-5-yl)-N-methyl-1H-indazole-7-carboxamide 613

¹H NMR (400 MHz, DMSO-d₆) δ 13.62 (s, 1H), 11.21 (s, 1H), 8.70 (d, J =7.2 Hz, 1H), 8.55 (s, 1H), 7.98 (s, 1H), 7.84 (s, 1H), 7.00-6.99 (m,2H), 5.03- 4.86 (m, 1H), 3.52 (s, 3H), 2.17-2.12 (m, 1H), 1.71-1.64 (m,1H), 1.21-1.14 (m, 1H); LCMS (electrospray) m/z 513.10 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-((5-fluoropyrimidin-2-yl)(methyl)amino)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 614

¹H NMR (400 MHz, DMSO-d₆) δ 13.75 (s, 1H), 11.20 (s, 1H), 8.71 (d, J =7.2 Hz, 1H), 8.22 (d, J = 6.8 Hz, 1H), 8.04 (s, 1H), 7.84 (s, 1H), 7.01(dd, J = 2.2, 7.0 Hz, 2H), 6.60 (d, J = 5.6 Hz, 1H), 5.06- 4.86 (m, 1H),3.41 (s, 3H), 2.19-2.12 (m, 1H), 1.73-1.63 (m, 1H), 1.21-1.17 (m, 1H);LCMS (electrospray) m/z 494.10 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(methyl(pyridin-4-yl)amino)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide615

¹H NMR (400 MHz, DMSO-d₆) δ 14.02 (s, 1H), 11.21 (s, 1H), 8.71 (d, J =7.2 Hz, 1H), 8.09 (s, 1H), 7.83 (s, 1H), 7.00 (s, 1H), 6.97 (s, J = 7.2Hz, 1H), 5.04-4.84 (m, 1H), 4.79 (dd, J = 18 Hz, 110 Hz, 2H), 2.18-2.11(m, 1H), 1.90 (s, 3H), 1.70-1.62 (m, 1H), 1.28-1.12 (m, 1H); LCMS(electrospray) m/z 484.1 (M + H)+. J (1S,2S)-N-(5-(5-chloro-7-(N-(cyanomethyl)acetamido)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 616

¹H NMR (400 MHz, DMSO-d₆) δ 13.51 (s, 1H), 11.19 (s, 1H), 8.66 (d, J =7.2 Hz, 1H), 8.38 (dd, J = 1.6, 4.4 Hz, 2H), 7.89 (s, 1H), 7.73-7.72 (m,1H), 7.21 (d, J = 6.0 Hz, 2H), 6.95 (s, 1H), 6.90 (dd, J = 2.4, 7.2 Hz,1H), 5.05-4.84 (m, 1H), 3.54 (t, 2H), 3.06 (d, J = 2.0 Hz, 3H), 2.86 (t,J = 7.4 Hz, 2H), 2.18-2.11 (m, 1H), 1.72-1.64 (m, 1H), 1.21- 1.13 (m,1H); LCMS (electrospray) m/z 522.10 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(methyl(2-(pyridin-4-yl)ethyl)amino)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 617

¹H NMR (400 MHz, DMSO-d₆) δ 13.70 (s, 1H), 11.21 (s, 1H), 8.91 (d, J =0.8 Hz, 1H), 8.71 (d, J = 7.2 Hz, 1H), 8.58 (d, J = 2.0 Hz, 1H), 8.01(s, 1H), 7.85 (s, 1H), 7.01-6.99 (m, 2H), 5.04-4.85 (m, 1H), 3.55 (s,3H), 2.18-2.11 (m, 1H), 1.71-1.64 (m, 1H), 1.21-1.14 (m, 1H); LCMS(electrospray) m/z 496.10 (M + H)+. J (1S,2S)-N-(5-(5-chloro-6-fluoro-7-(methyl(1,3,5-triazin-2-yl)amino)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 618

¹H NMR (400 MHz, DMSO-d₆) δ 13.67 (s, 1H), 11.21 (s, 1H), 8.88 (d, J =2.0 Hz, 1H), 8.71 (d, J = 7.2 Hz, 1H), 8.38 (s, 1H), 8.01 (s, 1H), 7.85(s, 1H), 7.01-6.99 (m, 2H), 5.05-4.84 (m, 1H), 3.63 (s, 3H), 2.18-2.11(m, 1H), 1.71-1.63 (m, 1H), 1.21- 1.11 (m, 1H); LCMS (electrospray) m/z496.10 (M + H)+. J (1S,2S)-N-(5-(5-chloro-6-fluoro-7-(methyl(1,2,4-triazin-3-yl)amino)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 619

¹H NMR (400 MHz, DMSO-d₆) δ 13.29 (s, 1H), 11.15 (s, 1H), 8.61 (d, J =7.3 Hz, 1H), 7.87 (s, 1H), 7.71 (s, 1H), 6.92-6.90 (m, 2H), 5.18-5.17(m, 1H), 5.03-4.85 (m, 1H), 4.03 (s, 1H), 2.17-2.09 (m, 1H), 1.72-1.62(m, 1H), 1.23 (d, J = 6.4 Hz, 6H), 1.20-1.15 (m, 1H); LCMS(electrospray) m/z 445.10 (M + H)+. J (1S,2S)-N-(5-(5-chloro-6-fluoro-7-(isopropylamino)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 620

¹H NMR (400 MHz, DMSO-d₆) δ 13.51 (s, 1H), 11.19 (s, 1H), 8.65 (d, J =7.2 Hz, 1H), 7.88 (s, 1H), 7.76 (s, 1H), 6.94 (s, 1H), 6.92 (s, J = 7.2Hz, 1H), 5.04-4.84 (m, 1H), 3.93 (t, J = 9.6 Hz, 1H), 2.84 (s, 3H),2.18-2.07 (m, 3H), 1.96-1.86 (m, 2H), 1.72-1.57 (m, 3H), 1.28-1.12 (m,1H); LCMS (electrospray) m/z 471.1 (M + H)+. J (1S,2S)-N-(5-(5-chloro-7-(cyclobutyl(methyl)amino)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 621

¹H NMR (400 MHz, DMSO-d₆) δ 13.81 (s, 1H), 11.21 (s, 1H), 8.69 (d, J =7.2 Hz, 1H), 7.88 (s, 1H), 7.81 (s, 1H), 6.97 (s, 1H), 6.95 (s, J = 7.2Hz, 1H), 5.04-4.84 (m, 1H), 3.02 (q, J = 7.3 Hz, 2H), 2.18- 2.08 (m,1H), 1.72-1.62 (m, 1H), 1.22-1.13 (m, 4H); LCMS (electrospray) m/z 448.1(M + H)+. J (1S,2S)-N-(5-(5-chloro-7-(ethylthio)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 622

¹H NMR (400 MHz, DMSO-d₆) δ 13.44 (s, 1H), 11.20 (s, 1H), 8.66 (d, J =7.2 Hz, 1H), 7.89 (s, 1H), 7.76 (d, J = 1.2 Hz, 1H), 6.95-6.93 (m, 2H),5.03- 4.84 (m, 1H), 3.56 (s, 1H), 2.89 (d, J = 3.6 Hz, 3H), 2.18-2.11(m, 1H), 1.72-1.62 (m, 1H), 1.22- 1.15 (m, 7H); LCMS (electrospray) m/z459.10 (M + H)+. J (1S,2S)-N-(5-(5-chloro-6-fluoro-7-(isopropyl(methyl)amino)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 623

¹H NMR (400 MHz, DMSO-d₆) δ 13.66 (s, 1H), 11.21 (s, 1H), 8.70 (d, J =7.2 Hz, 1H), 7.97 (s, 1H), 7.80 (m, 1H), 6.97-6.94 (m, 2H), 5.05-4.85(m, 1H), 3.84 (t, J = 7.8 Hz, 2H), 3.60 (t, J = 8.0 Hz, 2H), 2.82 (s,3H), 2.18-2.11 (m, 1H), 1.73-1.62 (m, 1H), 1.21-1.15 (m, 1H); LCMS(electrospray) m/z 486.10 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(3- methyl-2-oxoimidazolidin-1-yl)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 624

¹H NMR (400 MHz, DMSO-d₆) δ 13.13 (s, 1H), 11.17 (s, 1H), 8.62 (d, J =6.8 Hz, 1H), 7.86 (s, 1H), 7.69 (d, J = 0.8 Hz, 1H), 6.96-6.86 (m, 2H),5.05- 4.83 (m, 1H), 4.68-4.58 (m, 2H), 4.37-4.30 (m, 1H), 4.27-4.16 (m,2H), 3.27 (s, 3H), 2.18-2.09 (m, 1H), 1.73-1.61 (m, 1H), 1.20-1.12 (m,1H); LCMS (electrospray) m/z 473.1 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(3-methoxyazetidin-1-yl)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 625

¹H NMR (400 MHz, DMSO-d₆) δ 13.41 (s, 1H), 11.19 (s, 1H), 8.65 (d, J =7.2 Hz, 1H), 7.87 (s, 1H), 7.76 (s, 1H), 6.94 (s, 1H), 6.92 (s, J = 7.2Hz, 1H), 5.04-4.84 (m, 1H), 3.01-2.98 (m, 4H), 2.18-2.08 (m, 1H),1.72-1.62 (m, 1H), 1.22-1.13 (m, 4H), 0.63-0.60 (m, 2H), 0.49-0.45 (m,2H); LCMS (electrospray) m/z 457.1 (M + H)+. J (1S,2S)-N-(5-(5-chloro-7-(cyclopropyl(methyl)amino)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 626

¹H NMR (400 MHz, DMSO-d₆) δ 14.02 (s, 1H), 11.24 (s, 1H), 10.49 (s, 1H),8.73 (d, J = 7.2 Hz, 1H), 8.07 (s, 1H), 7.89-7.87 (m, 1H), 7.02 (s, 1H),7.00 (dd, J = 7.0, 1.8 Hz, 1H), 5.06-4.85 (m, 1H), 2.19-2.12 (m, 1H),1.73-1.63 (m, 1H), 1.21-1.15 (m, 1H); LCMS (electrospray) m/z 416.05(M + H+). J (1S,2S)-N-(5-(5-chloro-6-fluoro-7-formyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 627

¹H NMR (400 MHz, DMSO-d₆) δ 13.06 (s, 1H), 11.13 (s, 1H), 8.58 (d, J =6.8 Hz, 1H), 7.81 (s, 1H), 7.64 (s, 1H), 6.90-6.81 (m, 2H), 5.02-4.80(m, 1H), 4.49-4.40 (m, 2H), 4.20-4.04 (m, 2H), 3.53 (d, J = 6.4 Hz, 2H),3.25 (s, 3H), 2.99-2.88 (m, 1H), 2.15-2.04 (m, 1H), 1.68-1.57 (m, 1H),1.17- 1.09 (m, 1H); LCMS (electrospray) m/z 487.1 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(3- (methoxymethyl)azetidin-1-yl)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 628

¹H NMR (400 MHz, DMSO-d₆) δ 13.62 (s, 1H), 11.20 (s, 1H), 8.68 (d, J =7.2 Hz, 1H), 7.95 (d, J = 2.0 Hz, 1H), 7.74 (d, J = 1.2 Hz, 1H), 6.96(s, 1H), 6.91 (dd, J = 1.6, 7.2 Hz, 1H), 5.06-4.84 (m, 1H), 3.69-3.61(m, 4H), 3.47-3.39 (m, 4H), 2.18-2.10 (m, 1H), 1.73-1.61 (m, 1H),1.21-1.12 (m, 1H); LCMS (electrospray) m/z 521.1 (M + H)+. J(1S,2S)-N-(5-(5-chloro-7-(1,1- dioxidothiomorpholino)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 629

¹H NMR (400 MHz, DMSO-d₆) δ 13.57 (s, 1H), 11.20 (s, 1H), 10.49 (s, 1H),8.68 (d, J = 7.2 Hz, 1H), 8.07 (s, 1H), 7.89-7.87 (m, 1H), 7.02 (s, 1H),7.00 (dd, J = 7.0, 1.8 Hz, 1H), 5.06-4.85 (m, 1H), 2.19-2.12 (m, 1H),1.73-1.63 (m, 1H), 1.21-1.15 (m, 1H); LCMS (electrospray) m/z 416.05(M + H+). J (1S,2S)-N-(5-(5-chloro-6-fluoro-7-(hydroxymethyl)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 630

¹H NMR (400 MHz, DMSO-d₆) δ 13.41 (s, 1H), 11.19 (s, 1H), 8.61 (d, J =7.2 Hz, 1H), 7.91 (s, 1H), 7.76 (s, 1H), 6.94 (s, 1H), 6.87 (s, J = 7.2Hz, 1H), 5.04-4.84 (m, 1H), 4.55-4.51 (m, 2H), 3.98-3.94 (m, 2H),2.85-2.80 (m, 1H), 2.15-2.08 (m, 1H), 1.72-1.62 (m, 1H), 1.29-1.12 (m,4H), 0.86-0.79 (m, 1H); LCMS (electrospray) m/z 457.1 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(3- methylazetidin-1-yl)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 631

¹H NMR (400 MHz, DMSO-d₆) δ 13.49 (s, 1H), 11.19 (s, 1H), 8.66 (d, J =7.2 Hz, 1H), 7.91 (s, 1H), 7.74 (t, J = 1.2 Hz, 1H), 6.95 (s, 1H), 6.91(dd, J = 2.4, 7.2 Hz, 1H), 5.06-4.84 (m, 1H), 3.53-3.39 (m, 4H),2.90-2.82 (m, 4H), 2.19-2.09 (m, 1H), 1.73-1.61 (m, 1H), 1.21-1.12 (m,1H); LCMS (electrospray) m/z 489.1 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7- thiomorpholino-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 632

¹H NMR (400 MHz, DMSO-d₆) δ 13.41 (s, 1H), 11.20 (s, 1H), 8.61 (d, J =7.2 Hz, 1H), 7.96 (s, 1H), 7.68 (s, 1H), 6.92 (s, 1H), 6.87 (s, J = 7.2Hz, 1H), 5.04-4.84 (m, 1H), 4.55-4.44 (m, 4H), 2.15-2.08 (m, 1H),1.72-1.62 (m, 1H), 1.66 (d, J = 22 Hz, 1H), 1.29-1.12 (m, 1H); LCMS(electrospray) m/z 475.1 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(3-fluoro-3-methylazetidin-1-yl)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide633

¹H NMR (400 MHz, DMSO-d₆) δ 13.90 (br s, 1H), 11.23 (s, 1H), 8.71 (d, J= 7.2 Hz, 1H), 7.99 (d, J = 17.2 Hz, 1H), 7.85-7.83 (m, 1H), 7.00 (s,1H), 6.97 (dd, J = 7.0, 2.0 Hz, 1H), 5.06-4.85 (m, 1H), 2.18- 2.11 (m,1H), 1.73-1.63 (m, 1H), 1.21-1.14 (m, 1H); LCMS (electrospray) m/z439.05 (M + H+). J (1S,2S)-N-(5-(5-chloro-7-((E)-2-cyanovinyl)-6-fluoro-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 634

¹H NMR (400 MHz, DMSO-d₆) δ 13.91 (s, 1H), 11.22 (s, 1H), 8.70 (d, J =7.2 Hz, 1H), 7.99 (s, 1H), 7.83-7.80 (m, 1H), 6.98 (s, 1H), 6.96 (dd, J= 7.0, 1.8 Hz, 1H), 5.93 (s, 1H), 5.81 (s, 1H), 5.05-4.84 (m, 1H),2.18-2.11 (m, 1H), 1.72-1.62 (m, 1H), 1.20-1.13 (m, 1H); LCMS(electrospray) m/z 420.00 (M + H+). J (1S,2S)-N-(5-(5-chloro-6-fluoro-7-(fluoromethyl)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 635

¹H NMR (400 MHz, DMSO-d₆) δ 13.59 (s, 1H), 11.18 (s, 1H), 8.67 (d, J =7.1 Hz, 1H), 7.93 (s, 1H), 7.75 (t, J = 1.4 Hz, 1H), 6.96 (s, 1H), 6.92(dd, J = 7.1, 1.6 Hz, 1H), 5.08-4.80 (m, 1H), 3.89 (t, J = 11.5 Hz, 2H),3.32-3.24 (m, 2H), 3.24-3.10 (m, 2H), 2.97 (d, J = 11.5 Hz, 2H),2.22-2.09 (m, 1H), 1.77-1.61 (m, 1H), 1.22-1.11 (m, 1H); LCMS(electrospray) m/z 505.10 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(1- oxidothiomorpholino)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 636

¹H NMR (400 MHz, DMSO-d₆) δ 13.44 (s, 1H), 11.18 (s, 1H), 8.64 (d, J =7.1 Hz, 1H), 7.75 (s, 1H), 7.03-6.84 (m, 2H), 6.42 (s, 1H), 5.10-4.83(m, 1H), 4.83-4.49 (m, 2H), 2.24-2.04 (m, 1H), 1.76-1.59 (m, 1H),1.21-1.05 (m, 1H); LCMS (electrospray) m/z 442.10 (M + H)+. J(1S,2S)-N-(5-(5-chloro-7- ((cyanomethyl)amino)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 637

¹H NMR (400 MHz, DMSO-d₆) δ 13.63-14.10 (1H), 11.21 (s, 1H), 8.71 (d, J= 7.1 Hz, 1H), 8.09 (s, 1H), 7.82 (t, J = 1.4 Hz, 1H), 7.28 (s, 2H),6.99- 6.96 (m, 2H), 6.41 (t, J = 2.2 Hz, 2H), 5.06-4.85 (m, 1H),2.19-2.12 (m, 1H), 1.73-1.63 (m, 1H), 1.21-1.14 (m, 1H); LCMS(electrospray) m/z 453.10 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(1H-pyrrol-1-yl)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 638

¹H NMR (400 MHz, DMSO-d₆) δ 13.51 (s, 1H), 11.20 (s, 1H), 8.67 (d, J =7.1 Hz, 1H), 7.92 (s, 1H), 7.80 (d, J = 1.1 Hz, 1H), 7.02-6.87 (m, 2H),5.76 (s, 1H), 5.09-4.81 (m, 1H), 2.23-2.07 (m, 1H), 1.75-1.61 (m, 7H),1.21-1.10 (m, 2H); LCMS (electrospray) m/z 470.10 (M + H)+. J(1S,2S)-N-(5-(5-chloro-7-((2- cyanopropan-2-yl)amino)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 639

¹H NMR (400 MHz, DMSO-d₆) δ 13.67-13.30 (m, 1H), 11.18 (s, 1H), 8.68 (d,J = 7.1 Hz, 1H), 7.94 (s, 1H), 7.79 (d, J = 1.0 Hz, 1H), 7.05-6.79 (m,2H), 5.63 (s, 1H), 5.38 (s, 1H), 5.15-4.77 (m, 1H), 2.21 (s, 3H),2.18-2.09 (m, 1H), 1.74-1.60 (m, 1H), 1.25-1.12 (m, 1H); LCMS(electrospray) m/z 428.1 (M + H+). J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(prop-1-en-2-yl)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 640

¹H NMR (400 MHz, DMSO-d₆) δ 13.61 (br d, J = 2.1 Hz, 1H), 11.18 (s, 1H),8.66 (d, J = 7.2 Hz, 1H), 7.92 (s, 1H), 7.76 (d, J = 0.9 Hz, 1H),7.07-6.84 (m, 2H), 5.10-4.76 (m, 1H), 3.62 (td, J = 7.0, 14.1 Hz, 1H),2.15 (td, J = 6.9, 13.8 Hz, 1H), 1.76-1.59 (m, 1H), 1.44 (d, J = 7.0 Hz,6H), 1.18 (tdd, J = 6.2, 9.0, 12.3 Hz, 1H); LCMS (electrospray) m/z430.2 (M + H+). J (1S,2S)-N-(5-(5-chloro-6-fluoro-7-isopropyl-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 641

¹H NMR (400 MHz, DMSO-d₆) δ 13.32 (s, 1H), 11.03 (s, 1H), 8.61 (d, J =7.1 Hz, 1H), 7.95 (s, 1H), 7.73 (s, 1H), 6.98-6.88 (m, 2H), 6.24-5.96(m, 1H), 5.05-4.81 (m, 1H), 3.34-3.24 (m, 1H), 2.22-2.09 (m, 1H),1.78-1.58 (m, 4H), 1.22-1.11 (m, 1H); LCMS (electrospray) m/z 456.10(M + H)+. J (1S,2S)-N-(5-(5-chloro-7-((1-cyanoethyl)amino)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 642

¹H NMR (400 MHz, DMSO-d₆) δ 13.11 (s, 1H), 10.83 (s, 1H), 8.54 (d, J =7.1 Hz, 1H), 7.90-7.72 (m, 1H), 7.62 (s, 1H), 6.88 (s, 1H), 6.86-6.79(m, 1H), 5.56-5.24 (m, 1H), 5.00-4.74 (m, 1H), 4.34- 3.50 (m, 4H),2.38-2.03 (m, 3H), 1.75-1.56 (m, 1H), 1.19-1.04 (m, 1H); LCMS(electrospray) m/z 475.10 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(3-fluoropyrrolidin-1-yl)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 643

¹H NMR (400 MHz, DMSO-d₆) δ 13.83 (s, 1H), 11.08 (s, 1H), 8.67 (d, J =7.1 Hz, 1H), 7.99 (s, 1H), 7.82 (d, J = 5.5 Hz, 1H), 7.67-6.83 (m, 7H),5.59- 5.07 (m, 3H), 5.05-4.79 (m, 1H), 2.23-2.09 (m, 1H), 1.79-1.62 (m,2H), 1.43 (d, J = 7.1 Hz, 2H), 1.23-1.09 (m, 1H); LCMS (electrospray)m/z 591.20 (M + H)+. J benzyl (5-chloro-6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1- carboxamido)pyrazolo[1,5-a]pyridin-5-yl)-1H-indazol-7-yl)(1-cyanoethyl)carbamate 644

¹H NMR (400 MHz, DMSO-d₆) δ 11.21 (s, 1H), 8.72 (d, J = 7.2 Hz, 1H),8.07 (s, 1H), 7.87 (d, J = 1.0 Hz, 1H), 7.05-6.99 (m, 2H), 6.95 (br s,1H), 6.27 (t, J = 3.2 Hz, 1H), 6.16-6.11 (m, 1H), 5.08-4.84 (m, 1H),2.16 (td, J = 6.8, 14.1 Hz, 1H), 2.10-2.04 (m, 3H), 1.78-1.63 (m, 1H),1.23-1.15 (m, 1H); LCMS (electrospray) m/z 467.1 (M + H+). J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(2-methyl-1H-pyrrol-1-yl)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 645

¹H NMR (400 MHz, DMSO-d₆) δ 13.95-13.76 (m, 1H), 10.54 (s, 1H), 8.65 (d,J = 7.1 Hz, 1H), 8.47 (s, 1H), 7.98 (s, 1H), 7.76 (d, J = 1.0 Hz, 1H),6.91 (dd, J = 2.0, 7.1 Hz, 1H), 6.76 (s, 1H), 4.92- 4.85 (m, 1H),4.03-3.91 (m, 2H), 3.76 (dd, J = 1.3, 10.6 Hz, 1H), 2.57 (s, 3H),2.38-2.29 (m, 1H), 1.06 (d, J = 7.2 Hz, 3H); LCMS (electrospray) m/z476.1(M + H+). J (3S,4R)-4-methyltetrahydrofuran-3-yl (5-(5-chloro-6-fluoro-7-(methylthio)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2- yl)carbamate 646

¹H NMR (400 MHz, DMSO-d₆) δ 13.51 (s, 1H), 11.07 (s, 1H), 9.60-9.58 (m,1H), 8.64 (d, J = 7.1 Hz, 1H), 7.87 (s, 1H), 7.72 (s, 1H), 7.53 (s, 1H),7.28 (s, 1H), 6.94 (s, 1H), 6.90 (dd, J = 7.1, 1.8 Hz, 1H), 3.80 (s,3H), 2.99 (7H), 2.32 (dd, J = 9.1, 4.3 Hz, 2H), 2.00-1.95 (m, 1H),1.68-1.55 (m, 1H), 1.37-1.18 (m, 2H), 0.97 (d J = 6.2 Hz 3H). LCMS(electrospray) m/z 507.1 (M + H)+. J (1S,2R,3S)-N-(5-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-methyl- 3-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamide 647

¹H NMR (400 MHz, DMSO-d₆) δ 13.52 (s, 1H), 9.05 (s, 1H), 8.57 (d, J =7.0 Hz, 1H), 7.87 (s, 1H), 7.65 (dd, J = 1.77, 0.79 Hz, 1H), 6.85-6.81(m, 2H), 6.72 (s, 1H), 3.01 (s, 6H), 2.62-2.58 (m, 1H), 0.69- 0.65 (m,2H), 0.46-0.44 (m, 2H); LCMS (electrospray) m/z 428.0 (M + H)+. J1-(5-(5-chloro-7-(dimethylamino)-6- fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-3-cyclopropylurea 648

¹H NMR (400 MHz, DMSO-d₆) δ 11.03 (s, 1H), 8.63 (d, J = 7.2 Hz, 1H),8.55 (s, 1H), 7.87 (s, 1H), 7.71 (s, 1H), 7.53 (s, 1H), 7.26 (s, 1H),6.97 (s, 1H), 6.90 (dd , J = 7.1, 1.8 Hz, 1H), 3.77 (s, 3H), 3.02 (d, J= 2.2 Hz, 6H), 2.22-2.14 (m, 1H), 2.09 (d, J = 4.5 Hz, 3 H), 1.63-1.54(m, 1H), 1.26 (d, J = 6.1 Hz, 5H), 1.06 (t, J = 7.0 Hz, 2H); LCMS(electrospray) m/z 507.1 (M + H)+. J (1S,2S,3S)-N-(5-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-methyl- 3-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamide 649

¹H NMR (400 MHz, DMSO-d₆) δ 11.20 (s, 1H), 8.71 (d, J = 7.1 Hz, 1H),8.13 (s, 1H), 7.84-7.80 (m, 1H), 7.50-7.38 (m, 1H), 7.00 (s, 1H), 6.97(dd , J = 7.19, 1.94 Hz, 1 H), 6.66 (dd, J = 2.94, 1.69 Hz, 1 H),5.09-4.81 (m, 1H), 3.15-2.95 (m, 5H), 2.20- 2.11 (m, 1H), 1.75-1.61 (m,1H), 1.22-1.12 (m, 1H); LCMS (electrospray) m/z 524.1 (M + H)+. J1-(5-chloro-6-fluoro-4-(2-((1S,2S)-2- fluorocyclopropane-1-carboxamido)pyrazolo[1,5-a]pyridin-5-yl)-1H-indazol-7-yl)-N,N-dimethyl-1H- pyrrole-3-carboxamide 650

¹H NMR (400 MHz, DMSO-d₆) δ 14.17-13.20 (m, 1H), 11.17 (s, 1H), 8.66 (d,J = 7.2 Hz, 1H), 7.94 (s, 1H), 7.76 (s, 1H), 7.00-6.89 (m, 2H), 5.10-4.80 (m, 1H), 4.74 (br s, 1H), 2.15 (quin, J = 6.9 Hz, 1H), 1.77-1.59(m, 1H), 1.37 (d, J = 6.0 Hz, 6H), 1.26-1.09 (m, 1H); LCMS(electrospray) m/z 446.0 (M + H)+. J (1S,2S)-N-(5-(5-chloro-6-fluoro-7-isopropoxy-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 651

¹H NMR (400 MHz, DMSO-d₆) δ 13.55 (s, 1H), 11.19 (s, 1H), 8.67 (d, J =7.1 Hz, 1H), 7.90 (d, J = 1.1 Hz, 1H), 7.76 (t, J = 1.1 Hz, 1H),6.96-6.92 (m, 2H), 5.05-4.84 (m, 1H), 3.59 (q, J = 8.6 Hz, 1H),2.18-1.91 (m, 8H), 1.72-1.62 (m, 3H), 1.24-1.06 (m, 1H); LCMS(electrospray) m/z 456.1 (M + H)+. J(1S,2S)-N-(5-(5-chloro-7-cyclopentyl-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1- carboxamide 652

¹H NMR (400 MHz, DMSO-d₆) δ 13.35 (s, 1H), 11.15 (s, 1H), 8.65 (d, J =7.1 Hz, 1H), 7.90 (s, 1H), 7.79 (t, J = 1.4 Hz, 1H), 7.59 (s, 1H), 6.93(dd, J = 6.3, 2.5 Hz, 2H), 5.74 (t, J = 7.4 Hz, 1H), 5.01-4.80 (m, 1H),2.15-2.08 (m, 1H), 1.64 (dtd, J = 23.2, 6.9, 3.8 Hz, 1H), 1.17-1.10 (m,1H); LCMS (electrospray) m/z 487.1 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(2,2,2-trifluoro-1-hydroxyethyl)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 653

¹H NMR (400 MHz, DMSO-d₆) δ 13.25 (br s, 1H), 11.14 (s, 1H), 8.61 (d, J= 7.2 Hz, 1H), 7.85 (br s, 1H), 7.70 (s, 1H), 6.92 (s, 1H), 6.91-6.88(m, 1H), 5.32 (br d, J = 9.5 Hz, 1H), 5.06-4.82 (m, 1H), 2.21-2.06 (m,1H), 1.75-1.61 (m, 1H), 1.26 (d, J = 6.4 Hz, 3H), 1.21-1.14 (m, 1H),1.04 (br s, 1H), 0.48-0.35 (m, 2H), 0.34-0.18 (m, 2H); LCMS(electrospray) m/z 471.1 (M + H)+. J (1S,2S)-N-(5-(5-chloro-7-((1-cyclopropylethyl)amino)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 654

¹H NMR (400 MHz, DMSO-d₆) δ 13.26 (s, 1H), 11.15 (s, 1H), 8.61 (d, J =7.0 Hz, 1H), 7.85 (m, 1H), 7.70 (d, J = 1.0 Hz, 1H), 6.91 (m, 2H), 5.65(m, 1H), 4.95 (m, 1H), 3.31 (s, 2H), 2.14 (m, 1H), 1.67 (m, 1H), 1.18(m, 1H), 1.08 (m, 1H), 0.48 (d, J = 7.1 Hz, 2H), 0.27 (m, 2H); LCMS(electrospray) m/z 457.1 (M + H)+. J (1S,2S)-N-(5-(5-chloro-7-((cyclopropylmethyl)amino)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 655

¹H NMR (400 MHz, DMSO-d₆) δ13.56 (br s, 1H), 11.17 (s, 1H), 8.67 (d, J =7.1 Hz, 1H), 7.91 (s, 1H), 7.78 (s, 1H), 6.96 (br d, J = 2.2 Hz, 1H),6.95-6.91 (m, 1H), 5.07-4.82 (m, 1H), 3.85-3.74 (m, 2H), 3.67 (br s,1H), 3.25 (s, 3H), 2.21-2.09 (m, 1H), 1.74-1.60 (m, 1H), 1.40 (br d, J =6.1 Hz, 3H), 1.22-1.12 (m, 1H); LCMS (electrospray) m/z 460.1 (M + H)+.J (1S,2S)-N-(5-(5-chloro-6-fluoro-7-((R)-1-methoxypropan-2-yl)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 656

¹H NMR (400 MHz, DMSO-d₆) δ13.56 (br s, 1H), 11.17 (s, 1H), 8.67 (d, J =7.1 Hz, 1H), 7.91 (s, 1H), 7.78 (d, J = 1.0 Hz, 1H), 6.96 (d, J = 2.6Hz, 1H), 6.95-6.92 (m, 1H), 5.07-4.79 (m, 1H), 3.85-3.73 (m, 2H), 3.67(br s, 1H), 3.25 (s, 3H), 2.15 (td, J = 6.8, 13.7 Hz, 1H), 1.73-1.61 (m,1H), 1.40 (br d, J = 6.2 Hz, 3H), 1.18 (ddd, J = 2.8, 6.2, 12.3 Hz, 1H);LCMS (electrospray) m/z 460.1 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-((S)-1-methoxypropan-2-yl)-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 657

¹H NMR (400 MHz, DMSO-d₆) δ 13.15 (s, 1H), 11.15 (s, 1H), 8.62 (d, J =7.1 Hz, 1H), 8.04-7.83 (m, 1H), 7.71 (d, J = 1.0 Hz, 1H), 6.92 (s, 1H),6.90 (dd, J = 7.1, 2.0 Hz, 1H), 6.33-5.92 (m, 1H), 5.67- 5.51 (m, 1H),5.07-4.81 (m, 1H), 4.53-4.03 (m, 1H), 2.21-2.05 (m, 1H), 1.75-1.57 (m,1H), 1.32 (d, J = 6.6 Hz, 3H), 1.17 (ddt, J = 12.26, 9.07, 6.16, 6.16Hz, 1 H); LCMS (electrospray) m/z 481.0 (M + H)+. J(1S,2S)-N-(5-(5-chloro-7-((1,1- difluoropropan-2-yl)amino)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 658

¹H NMR (400 MHz, DMSO-d₆) δ 13.15 (s, 1H), 11.19 (s, 1H), 8.68 (d, J =7.1 Hz, 1H), 7.92 (s, 1H), 7.78 (d, J = 1.0 Hz, 1H), 6.98 (s, 1H), 6.94(dd, J = 2.0, 7.1 Hz, 1H), 5.57 (dd, J = 5.4, 10.8 Hz, 1H), 5.18 (d, J =3.4 Hz, 1H), 5.07-4.83 (m, 1H), 4.55 (dd, J = 3.7 Hz, 1H), 4.47 (dd, J =4.6, 8.9 Hz, 1H), 3.72 (dd, J = 1.2, 9.0 Hz, 1H), 2.26 (dd, J = 5.4,12.5 Hz, 1H), 2.20-2.02 (m, 2H), 1.76-1.62 (m, 1H), 1.28-1.12 (m, 2H);LCMS (electrospray) m/z 474.2 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(4-hydroxytetrahydrofuran-2-yl)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide659

¹H NMR (400 MHz, DMSO-d₆) δ13.80-13.56 (m, 1H), 11.18 (s, 1H), 8.77 (brd, J = 6.6 Hz, 1H), 8.67 (d, J = 7.1 Hz, 1H), 8.06 (s, 1H), 7.94 (s,1H), 7.77 (d, J = 0.9 Hz, 1H), 6.96 (s, 1H), 6.93 (dd, J = 1.8, 7.2 Hz,1H), 5.56 (br t, J = 7.2 Hz, 1H), 5.11-4.78 (m, 1H), 2.15 (td, J = 7.0,13.8 Hz, 1H), 1.73-1.62 (m, 1H), 1.58 (d, J = 7.2 Hz, 3H), 1.18 (tdd, J= 6.4, 9.0, 12.4 Hz, 1H); LCMS (electrospray) m/z 459.2 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(1- formamidoethyl)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 660

¹H NMR (400 MHz, DMSO-d₆) δ13.73-13.44 (m, 1H), 11.17 (s, 1H), 8.67 (d,J = 7.1 Hz, 1H), 8.46- 8.32 (m, 1H), 7.92 (s, 1H), 7.77 (s, 1H), 6.96(s, 1H), 6.93 (dd, J = 2.0, 7.2 Hz, 1H), 5.46 (br t, J = 7.0 Hz, 1H),5.09-4.77 (m, 1H), 2.20-2.07 (m, 3H), 1.78-1.61 (m, 1H), 1.55 (br d, J =7.2 Hz, 3H), 1.27-1.07 (m, 1H), 0.95 (t, J = 7.6 Hz, 3H); LCMS(electrospray) m/z 487.2 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(1- propionamidoethyl)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 661

¹H NMR (400 MHz, DMSO-d₆) δ13.77-13.42 (m, 1H), 11.18 (s, 1H), 8.67 (d,J = 7.1 Hz, 1H), 8.54- 8.48 (m, 1H), 8.34 (br s, 1H), 7.91 (s, 1H), 7.77(d, J = 0.7 Hz, 1H), 6.95 (s, 1H), 6.93 (dd, J = 2.0, 7.2 Hz, 1H), 5.45(br t, J = 7.1 Hz, 1H), 5.05-4.83 (m, 1H), 3.08 (br t, J = 8.3 Hz, 1H),2.19-2.01 (m, 3H), 1.99-1.83 (m, 3H), 1.75-1.61 (m, 2H), 1.55 (d, J =7.2 Hz, 3H), 1.17 (ddd, J = 2.8, 6.1, 12.3 Hz, 1H); LCMS (electrospray)m/z 513.2 (M + H)+. J N-(1-(5-chloro-6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1- carboxamido)pyrazolo[1,5-a]pyridin-5-yl)-1H-indazol-7- yl)ethyl)cyclobutanecarboxamide 662

¹H NMR (400 MHz, DMSO-d₆) δ14.24-12.89 (m, 1H), 11.19 (s, 1H),10.54-9.82 (m, 1H), 8.68 (d, J = 7.0 Hz, 1H), 7.97 (s, 1H), 7.00-6.92(m, 2H), 5.56 (q, J = 7.0 Hz, 1H), 5.07-4.81 (m, 1H), 2.21- 2.08 (m,1H), 1.69 (d, J = 7.0 Hz, 3H), 1.66-1.60 (m, 1H), 1.26-1.09 (m, 1H);LCMS (electrospray) m/z 527.1 (M + H)+. J(1S,2S)-N-(5-(5-chloro-6-fluoro-7-(1-(2,2,2-trifluoroacetamido)ethyl)-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 663

¹H NMR (400 MHz, DMSO-d₆) δ13.90-13.44 (m, 1H), 11.21-11.13 (m, 1H),8.94-8.80 (m, 1H), 8.66 (d, J = 7.2 Hz, 1H), 8.56 (s, 1H), 7.96-7.86 (m,1H), 7.80-7.73 (m, 1H), 6.95 (s, 1H), 6.94-6.91 (m, 1H), 5.54-5.41 (m,1H), 4.93 (s, 1H), 2.22-2.09 (m, 1H), 1.90-1.82 (m, 3H), 1.73-1.61 (m,1H), 1.54 (d, J = 7.0 Hz, 3H), 1.21-1.13 (m, 1H); LCMS (electrospray)m/z 473.1 (M + H)+. J (1S,2S)-N-(5-(7-(1-acetamidoethyl)-5-chloro-6-fluoro-1H-indazol-4- yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 664

¹H NMR (400 MHz, DMSO-d₆) δ 13.73 (s, 1H), 11.21 (s, 1H), 8.70 (d, J =7.1 Hz, 1H), 7.97 (s, 1H), 7.77 (s, 1H), 7.00 (s, 1H), 6.93 (dd, J =7.1, 2.2 Hz, 1H), 6.40 (s, 1H), 5.05-4.85 (m, 1H), 3.20 (s, 3H), 2.58(d, J = 4.4 Hz, 3H), 2.18-2.11 (m, 1H), 1.72- 1.64 (m, 1H), 1.21-1.15(m, 1H) m/z 474.10 (M + H)+. J (1S,2S)-N-(5-(5-chloro-7-(1,3-dimethylureido)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide 665

¹H NMR (400 MHz, DMSO-d₆) δ 14.06-13.53 (m, 1H), 11.18 (s, 1H),9.82-9.45 (m, 1H), 8.67 (d, J = 7.1 Hz, 1H), 7.95 (s, 1H), 7.78 (d, J =0.9 Hz, 1H), 6.99-6.91 (m, 2H), 6.44-6.11 (m, 1H), 5.61-5.51 (m, 1H),5.05-4.83 (m, 1H), 2.15 (td, J = 7.0, 13.8 Hz, 1H), 1.70 (dt, J = 3.7,6.9 Hz, 1H), 1.65 (d, J = 7.2 Hz, 3H), 1.24-1.12 (m, 1H); LCMS(electrospray) m/z 509.2 (M + H)+. J (1S,2S)-N-(5-(5-chloro-7-(1-(2,2-difluoroacetamido)ethyl)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide 666

¹H NMR (400 MHz, DMSO-d₆) δ 13.33 (s, 1H), 11.20 (s, 1H), 8.67 (t, J =8.0 Hz, 1H), 7.91 (s, 1H), 7.82 (t, J = 1.1 Hz, 1H), 6.97 (dd, J = 7.1,2.2 Hz, 2H), 5.04-4.85 (m, 2H), 3.90 (t, J = 6.3 Hz, 1H), 3.38 (d, J =6.6 Hz, 3H), 3.25 (s, 3H), 2.14 (t, J = 8.0 Hz, 1H), 1.71-1.64 (m, 1H),1.18 (dd, J = 12.1, 8.8 Hz, 1H), 0.95 (d, J = 6.6 Hz, 3H); LCMS(electrospray) m/z 490.1 (M + H)+. J(1S,2S)-N-(5-(5-chloro-7-((1S,2R)-1,2-dimethoxypropyl)-6-fluoro-1H-indazol-4-yl)pyrazolo[1,5-a]pyridin-2-yl)-2- fluorocyclopropane-1-carboxamide

Evaluation of Compounds

HPK1 Kinase Assay

HPK1 kinase activity was measured by Promega's ADP-Glo™ kinase assay. Inthis assay, 5 ng of recombinant human HPK1 (signalchem) is incubatedwith 5 μL of compounds (0.5% DMSO), 5 μL of MBP (0.5 μg/μl) and 5 μL ofATP (25 μM) in buffer (40 mM Tris, 7.5; 20 mM MgCl₂; 0.1 mg/ml BSA; 5 μMDTT). The assay was started by incubating the reaction mixture in a96-well plate at 30′ C for 40 minutes. After the incubation, 25 uLADP-Glo reagent was added and the reaction was incubated at roomtemperature for 40-min to stop the reaction and degrade residual ATP.The ADP product was then converted to ATP by adding 50 uL per well ofdetection reagent. Luminescence was detected after 30-min roomtemperature incubation with the Molecular device I3X plate reader. TheIC₅₀ values were calculated from a series of percent inhibition valuesdetermined at a range of inhibitor concentration using software routinesas implemented in the GraphPad Prism 7 software and SigmaPlot13.0.

Table 2 shows IC₅₀ values of the invented compounds which represent +for >1000 nM, ++ for 501-1000 nM, +++ for 101-500 nM, ++++ for <100 nM.

TABLE 2 In vitro activity against HPK1 data Example HPK1 IC₅₀ (nM) 1 +++2 +++ 3 + 4 ++ 5 +++ 6 +++ 7 +++ 8 + 9 + 10 + 11 ++ 12 + 13 + 14 + 15+++ 16 +++ 17 +++ 18 + 19 + 20 + 21 + 22 + 23 + 24 +++ 25 ++ 26 + 27 +28 +++ 29 +++ 30 +++ 31 + 32 +++ 33 +++ 34 + 35 +++ 36 +++ 37 +++ 38 +39 +++ 40 ++++ 41 +++ 42 +++ 43 ++++ 44 ++ 45 + 46 ++++ 47 ++++ 48 ++++49 ++ 50 ++++ 51 ++++ 52 + 53 +++ 54 + 55 +++ 56 ++++ 57 ++++ 58 ++++ 59++++ 60 + 61 ++++ 62 +++ 63 ++++ 64 ++++ 65 ++++ 66 ++++ 67 ++++ 68 ++++69 ++++ 70 ++++ 71 ++++ 72 +++ 73 ++++ 74 +++ 75 +++ 76 +++ 77 ++++ 78+++ 79 ++++ 80 ++++ 81 ++++ 82 ++++ 83 +++ 84 ++++ 85 ++++ 86 ++++ 87++++ 88 ++++ 89 ++++ 90 ++++ 91 +++ 92 ++++ 93 ++++ 94 ++++ 95 ++++ 96++++ 97 ++++ 98 ++++ 99 ++++ 100 ++++ 101 ++++ 102 ++++ 103 ++++ 104++++ 105 ++++ 106 ++++ 107 ++++ 108 ++++ 109 ++++ 110 ++++ 111 ++++ 112+++ 113 ++++ 114 +++ 115 ++++ 116 ++++ 117 ++++ 118 ++++ 119 +++ 120++++ 121 + 122 ++++ 123 ++++ 124 + 125 ++++ 126 ++++ 127 ++++ 128 +++129 ++++ 130 ++++ 131 +++ 132 +++ 133 ++++ 134 ++++ 135 + 136 ++++ 137++++ 138 ++++ 139 ++++ 140 + 141 + 142 + 143 ++++ 144 +++ 145 + 146 +++147 ++++ 148 + 149 ++++ 150 ++++ 151 + 152 ++++ 153 ++++ 154 ++++ 155++++ 156 ++++ 157 +++ 158 +++ 159 ++++ 160 ++++ 161 ++++ 162 ++++ 163++++ 164 + 165 ++++ 166 ++++ 167 ++++ 168 +++ 169 ++++ 170 ++++ 171 +172 ++++ 173 ++++ 174 ++++ 175 ++++ 176 ++++ 177 +++ 178 ++++ 179 ++++180 +++ 181 +++ 182 + 183 ++++ 184 ++++ 185 +++ 186 ++++ 187 ++++ 188 +189 ++++ 190 ++++ 191 ++++ 192 ++++ 193 ++++ 194 ++++ 195 +++ 196 ++++197 ++++ 198 ++++ 199 ++++ 200 ++++ 201 + 202 ++++ 203 ++++ 204 ++++ 205++++ 206 +++ 207 ++++ 208 ++++ 209 ++++ 210 ++++ 211 ++++ 212 + 213 +214 + 215 + 216 + 217 ++++ 218 ++++ 219 +++ 220 + 221 +++ 222 ++ 223++++ 224 +++ 225 + 226 ++++ 227 + 228 + 229 ++++ 230 + 231 + 232 ++++233 ++ 234 + 235 ++++ 236 ++++ 237 ++++ 238 ++++ 239 ++++ 240 ++ 241 +242 +++ 243 ++++ 244 +++ 245 ++++ 246 ++++ 247 ++++ 248 ++++ 249 +++ 250++++ 251 + 252 ++++ 253 ++++ 254 ++++ 255 ++++ 256 ++++ 257 ++++ 258++++ 259 + 260 ++++ 261 ++++ 262 ++++ 263 ++++ 264 ++++ 265 ++++ 266++++ 267 +++ 268 ++++ 269 ++++ 270 +++ 271 ++++ 272 ++++ 273 ++++ 274++++ 275 ++++ 276 ++++ 277 +++ 278 + 279 ++++ 280 ++++ 281 ++++ 282 ++++283 ++++ 284 +++ 285 ++++ 286 + 287 ++++ 288 ++++ 289 + 290 ++++ 291++++ 292 ++++ 293 ++++ 294 ++++ 295 ++++ 296 ++++ 297 ++++ 298 ++++ 299+++ 300 ++++ 301 ++++ 302 +++ 303 ++++ 304 ++++ 305 ++++ 306 ++++ 307++++ 308 +++ 309 ++++ 310 ++++ 311 ++++ 312 ++++ 313 + 314 + 315 ++++316 ++++ 317 ++++ 318 ++++ 319 ++++ 320 ++++ 321 ++++ 322 +++ 323 ++++324 ++++ 325 + 326 ++++ 327 ++++ 328 ++++ 329 ++++ 330 ++++ 331 ++++ 332++++ 333 ++++ 334 ++++ 335 ++++ 336 ++++ 337 ++++ 338 +++ 339 ++++ 340+++ 341 ++++ 342 ++++ 343 ++++ 344 +++ 345 ++++ 346 ++++ 347 ++++ 348++++ 349 ++++ 350 ++++ 351 ++++ 352 +++ 353 ++++ 354 + 355 + 356 ++++357 ++++ 358 ++++ 359 ++++ 360 ++++ 361 ++++ 362 ++++ 363 ++++ 364 ++++365 ++++ 366 ++++ 367 ++++ 368 ++++ 369 ++++ 370 ++++ 371 ++++ 372 ++++373 ++++ 374 ++++ 375 ++++ 376 ++++ 377 ++++ 378 ++++ 379 ++++ 380 ++++381 ++++ 382 +++ 383 ++++ 384 ++++ 385 ++++ 386 ++++ 387 ++++ 388 ++++389 ++++ 390 ++++ 391 ++++ 392 ++++ 393 ++++ 394 ++++ 395 ++++ 396 ++++397 ++++ 398 ++++ 399 ++++ 400 ++++ 401 ++++ 402 +++ 403 + 404 ++++ 405++++ 406 ++++ 407 ++++ 408 ++++ 409 ++++ 410 ++++ 411 ++++ 412 ++++ 413++++ 414 ++++ 415 ++++ 416 ++++ 417 ++++ 418 ++++ 419 ++++ 420 ++++ 421++++ 422 ++++ 423 ++++ 424 ++++ 425 ++++ 426 ++++ 427 ++++ 428 ++++ 429++++ 430 ++++ 431 +++ 432 ++++ 433 ++++ 434 ++++ 435 ++++ 436 ++++ 437++++ 438 ++++ 439 ++++ 440 ++++ 441 ++++ 442 ++++ 443 ++++ 444 ++++ 445++++ 446 ++++ 447 ++++ 448 ++++ 449 +++ 450 + 451 ++++ 452 ++++ 453 ++454 +++ 455 ++++ 456 ++ 457 ++++ 458 ++++ 459 +++ 460 ++++ 461 + 462++++ 463 ++++ 464 ++++ 465 ++++ 466 ++++ 467 ++++ 468 ++++ 469 ++++ 470+++ 471 +++ 472 + 473 + 474 +++ 475 + 476 ++++ 477 ++++ 478 ++ 479 ++++480 ++++ 481 ++++ 482 ++++ 483 ++++ 484 ++++ 485 ++++ 486 ++++ 487 ++++488 ++++ 489 ++++ 490 ++++ 491 ++++ 492 ++++ 493 ++++ 494 ++++ 495 ++++496 ++++ 497 ++++ 498 ++++ 499 ++++ 500 +++ 501 ++++ 502 ++++ 503 ++++504 ++++ 505 ++++ 506 ++++ 507 ++++ 508 ++++ 509 ++++ 510 ++++ 511 ++++512 ++++ 513 ++++ 514 ++++ 515 ++++ 516 ++++ 517 ++++ 518 ++++ 519 ++++520 ++++ 521 ++++ 522 ++++ 523 ++++ 524 ++++ 525 ++++ 526 ++++ 527 ++++528 ++++ 529 ++++ 530 ++++ 531 ++++ 532 ++++ 533 ++++ 534 ++++ 535 ++++536 ++++ 537 ++++ 538 ++++ 539 ++++ 540 ++++ 541 ++++ 542 ++++ 543 ++++544 ++++ 545 ++++ 546 ++++ 547 ++++ 548 ++++ 549 + 550 ++++ 551 + 552++++ 553 ++++ 554 ++++ 555 ++++ 556 ++++ 557 ++++ 558 ++++ 559 ++++ 560++++ 561 ++++ 562 ++++ 563 ++++ 564 ++++ 565 ++++ 566 +++ 567 ++++ 568++++ 569 ++++ 570 ++++ 571 ++++ 572 ++++ 573 ++++ 574 ++++ 575 ++++576 + 577 ++++ 578 ++++ 579 ++++ 580 ++++ 581 ++++ 582 ++++ 583 ++++ 584+++ 585 ++++ 586 ++++ 587 ++++ 588 ++++ 589 ++++ 590 ++++ 591 ++++ 592++++ 593 ++++ 594 ++++ 595 +++ 596 ++++ 597 ++++ 598 ++++ 599 ++++ 600++++ 601 ++++ 602 ++++ 603 ++++ 604 +++ 605 + 606 ++++ 607 ++++ 608 ++++609 ++++ 610 ++++ 611 ++++ 612 ++++ 613 ++++ 614 ++++ 615 ++++ 616 ++++617 ++++ 618 ++++ 619 ++++ 620 ++++ 621 ++++ 622 ++++ 623 ++++ 624 ++++625 ++++ 626 ++++ 627 ++++ 628 ++++ 629 ++++ 630 ++++ 631 ++++ 632 ++++633 ++++ 634 ++++ 635 ++++ 636 ++++ 637 ++++ 638 ++++ 639 ++++ 640 ++++641 ++++ 642 ++++ 643 +++ 644 ++++ 645 ++++ 646 ++++ 647 ++++ 648 ++++649 ++++ 650 ++++ 651 ++++ 652 ++++ 653 ++++ 654 ++++ 655 ++++ 656 ++++657 ++++ 658 ++++ 659 ++++ 660 ++++ 661 ++++ 662 ++++ 663 ++++ 664 ++++665 ++++ 666 +++

IFNγ and IL-2 Analysis of Human Peripheral Pan T Cells

Human peripheral blood pan T cells were purchased from STEMCELL™Technologies Inc. Human peripheral blood pan T cells were thawed andsuspended in DMEM media (10% FBS and 10 Penicillin/Streptomycin). 8×10⁴T cells were seeded in 96-well plate and incubated with variousconcentration of compounds and 100 nM Prostaglandin E2 for 1 hr. T cellswere stimulated with Dynabeads Human T-Activator CD3/CD28 (LifeTechnologies) at a 1:3 cells: beads ratio. Cytokine secretion wasmeasured after 24 hr post stimulation using MSD V-PLEX human cytokinekit as suggested by the manufacturer. Data were analyzed with an MESOQuickplex SQ120 (Mesoscale Discovery).

In Table 3, the values represent + for >1000 nM, ++ 200-1,000 nM, +++for <200 nM and − for not determined.

TABLE 3 IFNγ and IL-2 secretion of the invented compounds in humanperipheral blood pan T cells Example IFNγ (EC₅₀) IL-2 (EC₅₀) 104 ++ +105 ++ + 107 ++ − 110 +++ − 111 ++ − 118 +++ − 123 ++ + 125 +++ − 134+++ + 152 ++ ++ 156 ++ ++ 161 ++ − 162 ++ − 163 − − 167 ++ + 169 ++ +170 ++ + 172 ++ − 173 ++ − 174 ++ − 175 +++ − 178 − − 184 +++ − 193 ++ +194 ++ − 196 ++ − 199 ++ − 258 +++ ++ 291 +++ ++ 293 +++ − 296 +++ ++297 +++ +++ 316 ++ + 320 ++ − 324 +++ ++ 326 ++ ++ 327 +++ ++ 329 ++ ++330 ++ ++ 332 ++ ++ 333 ++ ++ 334 ++ ++ 359 ++ ++ 361 ++ + 484 +++ ++488 ++ − 503 ++ − 509 +++ ++ 520 ++ − 521 +++ +++ 523 +++ − 524 +++ +++525 +++ ++ 529 +++ +++ 530 ++ ++ 531 +++ ++ 532 ++ − 534 +++ − 541 ++ −543 +++ ++ 548 − − 550 ++ ++ 552 ++ ++ 556 +++ ++ 557 +++ ++ 558 +++ ++561 ++ ++ 562 ++ − 563 ++ ++ 564 ++ ++ 565 ++ ++ 569 ++ + 570 +++ ++ 574++ ++ 577 +++ ++ 579 +++ + 588 +++ +++

The invention claimed is:
 1. A compound of Formula (I):

or a pharmaceutically acceptable salt, hydrate, or solvate, thereof,wherein: X is O or S; L is a bond, —O—, —S—, or —NR⁶—; R¹ is alkyl,cycloalkyl, aryl, heteroaryl, or heterocyclyl, wherein R¹ is optionallysubstituted with one or more substituents independently selected fromR⁷; R⁶ is —H or C₁₋₆ alkyl; R⁷ is C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆alkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, halo, oxo, cyano,hydroxy, —C(O)R⁹, —C(O)OR⁹, —C(O)NR¹⁰R¹¹, —OR⁹, —OC(O)R⁹, —OC(O)NR¹⁰R¹¹,—SR⁹, —S(O)R⁹, —S(O)₂R⁹, —S(O)(═NH)R¹⁰, —S(O)₂NR¹⁰R¹¹, —NR¹⁰R¹¹,—N(R⁶)NR¹⁰R¹¹, —N(R⁶)OR⁹, —N(R⁶)C(O)R⁹, —N(R⁶)C(O)OR⁹,—N(R⁶)C(O)NR¹⁰R¹¹, —N(R⁶)S(O)₂R⁹, —N(R⁶)S(O)₂NR¹⁰R¹¹, or —P(O)R¹²R¹³; R⁹is —H, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl,cycloalkyl, aryl, heteroaryl, or heterocyclyl; Each R¹⁰ and R¹¹ isindependently —H, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, cycloalkyl,aryl, heteroaryl, or heterocyclyl, or R¹⁰ and R¹¹ are taken togetherwith the nitrogen atom to which they are attached to form a 4- to12-membered heterocyclyl optionally substituted with one or more groupsselected from the group consisting of halo, hydroxyl, alkyl, alkenyl,alkynyl, haloalkyl, hydroxyalkyl, —CN, —NO₂, —NR¹⁰R¹¹, —NR¹⁰C(═O)R⁹,—NR¹⁰C(═O)NR¹⁰R¹¹, —NR¹⁰C(═O)OR⁹, —OR⁹, —C(═O)R⁹, —C(═O)OR⁹,—C(═O)NR¹⁰R¹¹, —OC(═O)R⁹, —OC(═O)OR⁹, and —OC(═O)NR¹⁰R¹¹; Each R¹² andR¹³ is independently C₁₋₆ alkyl, C₁₋₆ alkoxy, C₃₋₈ cycloalkyl, aryl,heteroaryl, heterocyclyl, or R¹² and R¹³ are taken together with thephosphorus atom to which they are attached to form a 4- to 8-memberedheterocyclyl optionally substituted with one or more groups selectedfrom the group consisting of halo, hydroxyl, alkyl, alkenyl, alkynyl,haloalkyl, hydroxyalkyl, —CN, —NO₂, —NR¹⁰R¹¹, —NR¹⁰C(═O)R⁹,—NR¹⁰C(═O)NR¹⁰R¹¹, —NR¹⁰C(═O)OR⁹, —OR⁹, —C(═O)R⁹, —C(═O)OR⁹,—C(═O)NR¹⁰R¹¹, —OC(═O)R⁹, —OC(═O)OR⁹, and —OC(═O)NR¹⁰R¹¹; Het isselected from the group consisting of:

Each of R^(a), R^(b) and R^(c) is independently —H, -D, halo, CF₃, CF₂H,CH₂F, CN, OR⁹ or NR¹⁰R¹¹; R² is —H, -D, —CD₃, C₁₋₆ alkyl, C₂₋₆ alkenyl,C₂₋₆ alkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, halo,hydroxyl, —CD₂OH, —CN, —NO₂, haloalkyl, trimethylsilylethoxymethyl,—C(O)R⁹, —C(O)OR⁹, —C(O)NR¹⁰R¹¹, —OR⁹, —OC(O)R⁹, —OC(O)NR¹⁰R¹¹, —SR⁹,—S(O)R⁹, —S(O)₂R⁹, —S(O)(═NH)R¹⁰, —S(O)₂NR¹⁰R¹¹, —NR¹⁰R¹¹,—N(R⁶)NR¹⁰R¹¹, —N(R⁶)OR⁹, —N(R⁶)C(O)R⁹, —N(R⁶)C(O)R⁹, —N(R⁶)C(O)OR⁹,—N(R⁶)C(O)NR¹⁰R¹¹, —N(R⁶)S(O)₂R⁹, —N(R⁶)S(O)₂NR¹⁰R¹¹, or —P(O)R¹²R¹³,wherein the C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, cycloalkyl, aryl,heteroaryl, or heterocyclyl is optionally substituted with one or moregroups selected from the group consisting of halo, hydroxyl, alkyl,alkenyl, alkynyl, haloalkyl, hydroxyalkyl, —CN, —NO₂, —NR¹⁰R¹¹,—NR¹⁰C(═O)R⁹, —NR¹⁰C(═O)NR¹⁰R¹¹, —NR¹⁰C(═O)OR⁹, —OR⁹, —C(═O)R⁹,—C(═O)OR⁹, —C(═O)NR¹⁰R¹¹, —OC(═O)R⁹, —OC(═O)OR⁹, and —OC(═O)NR¹⁰R¹¹; R³is —H, -D, —CD₃, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, cycloalkyl,aryl, heteroaryl, heterocyclyl, halo, cyano, hydroxy, —CH₂OH, —CD₂OH,—OH, —CN, —NO₂, haloalkyl, —C(O)R⁹, —C(O)OR⁹, —C(O)NR¹⁰R¹¹, —OR⁹,—OC(O)R⁹, —OC(O)NR¹⁰R¹¹, —SR⁹, —S(O)R⁹, —S(O)₂R⁹, —S(O)(═NH)R¹⁰,—S(O)₂NR¹⁰R¹¹, —NR¹⁰R¹¹, —N(R⁶)NR¹⁰R¹¹, —N(R⁶)OR⁹, —N(R⁶)C(O)R⁹,—N(R⁶)C(O)OR⁹, —N(R⁶)C(O)NR¹⁰R¹¹, —N(R⁶)S(O)₂R⁹, —N(R⁶)S(O)₂NR¹⁰R¹¹, or—P(O)R¹²R¹³; M is a bond, —O—, —S—, or —NR⁶—; R⁶ is —H or C₁₋₆ alkyl; R⁴is —H, -D, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, cycloalkyl, aryl,heteroaryl, heterocyclyl, halo, cyano, hydroxy, —C(O)R⁹, —C(O)OR⁹,—C(O)NR¹⁰R¹¹, —S(O)₂R⁹, —S(O)(═NH)R¹⁰, —S(O)₂NR¹⁰R¹¹, or —P(O)R¹²R¹³,wherein C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, cycloalkyl, aryl,heteroaryl, or heterocyclyl is optionally substituted with one or moregroups selected from the group consisting of halo, hydroxyl, alkyl,alkenyl, alkynyl, haloalkyl, hydroxyalkyl, —CN, —CD₃, —NO₂, —NR¹⁰R¹¹,—NR¹⁰C(═O)R⁹, —NR¹⁰C(═O)NR¹⁰R¹¹, —NR¹⁰C(═O)OR⁹, —NR¹⁰S(O)₂R⁹, —OR⁹,—C(═O)R⁹, —C(═O)OR⁹, —C(═O)NR¹⁰R¹¹, —OC(═O)R⁹, —OC(═O)OR⁹, and—OC(═O)NR¹⁰R¹¹; and R⁵ is —H, -D, —CD₃, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆alkynyl, cycloalkyl, halo, hydroxyl, —CH₂OH, —CD₂OH, —CN or haloalkyl.2. The compound of claim 1 or a pharmaceutically acceptable saltthereof, wherein L is a bond, and R¹ is cycloalkyl which is optionallysubstituted with one or more groups selected from the group consistingof C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, cycloalkyl, halo, cyano,hydroxy, —C(O)R⁹, —C(O)OR⁹, —C(O)NR¹⁰R¹¹, —OR⁹, —OC(O)R⁹, —OC(O)NR¹⁰R¹¹,—NR¹⁰R¹¹, —N(R⁶)NR¹⁰R¹¹, —N(R⁶)OR⁹, —N(R⁶)C(O)R⁹, —N(R⁶)C(O)OR⁹, and—N(R⁶)C(O)NR¹⁰R¹¹.
 3. The compound of claim 1 or a pharmaceuticallyacceptable salt thereof, wherein each of R² and R³ is independently —H,halo, alkylthio, haloalkyl, or alkyl.
 4. The compound of claim 1 or apharmaceutically acceptable salt thereof, wherein M is a bond, —O—, or—NR⁶—; and R⁴ is —H, -D, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl,cycloalkyl, aryl, heteroaryl, heterocyclyl, halo, cyano, hydroxy,—C(O)R⁹, —C(O)NR¹⁰R¹¹, —S(O)₂R⁹, —S(O)(═NH)R¹⁰, or —S(O)₂NR¹⁰R¹¹,wherein the C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, cycloalkyl, aryl,heteroaryl, or heterocyclyl is optionally substituted with one or moregroups selected from the group consisting of halo, hydroxy, alkyl,alkenyl, alkynyl, haloalkyl, hydroxyalkyl, —CN, —CD₃, —NR¹⁰R¹¹,—NR¹⁰S(O)₂R⁹, and —NR¹⁰C(═O)R⁹.
 5. The compound of claim 1 or apharmaceutically acceptable salt thereof, which is a compound of Formula(II):


6. (canceled)
 7. (canceled)
 8. (canceled)
 9. The compound of claim 1 ora pharmaceutically acceptable salt thereof, which is a compound ofFormula (III):


10. (canceled)
 11. (canceled)
 12. (canceled)
 13. The compound of claim 1or a pharmaceutically acceptable salt thereof, which is a compound ofFormula (IV):


14. (canceled)
 15. (canceled)
 16. The compound of claim 1 or apharmaceutically acceptable salt thereof, which is a compound of Formula(V):


17. The compound of claim 16 or a pharmaceutically acceptable saltthereof, wherein L is a bond, and R¹ is cycloalkyl which is optionallysubstituted with one or more groups selected from the group consistingof C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, cycloalkyl, halo, cyano,hydroxy, —C(O)R⁹, —C(O)OR⁹, —C(O)NR¹⁰R¹¹, —OR⁹, —OC(O)R⁹, —OC(O)NR¹⁰R¹¹,—NR¹⁰R¹¹, —N(R⁶)NR¹⁰R¹¹, —N(R⁶)OR⁹, —N(R⁶)C(O)R⁹, —N(R⁶)C(O)OR⁹, and—N(R⁶)C(O)NR¹⁰R¹¹.
 18. The compound of claim 16 or a pharmaceuticallyacceptable salt thereof, wherein R¹ is cycloalkyl which is optionallysubstituted with one or more groups selected from the group consistingof halo, C₁₋₃ alkyl, C₁₋₃ hydroxyalkyl and C₁₋₃ haloalkyl.
 19. Thecompound of claim 16 or a pharmaceutically acceptable salt thereof,which is selected from the group consisting of the compound of Examples221-445 of Table
 1. 20. The compound of claim 16 or a pharmaceuticallyacceptable salt thereof, wherein R¹ is cyclopropyl which is optionallysubstituted with one or more groups selected from the group consistingof halo, C₁-C₃ alkyl, C₁-C₃ hydroxyalkyl and C₁-C₃ haloalkyl; R² is —H,alkyl, alkylthio, haloalkyl, or halo; R³ is —H, alkyl, or halo; M is abond, —O—, or —NR⁶—; R⁴ is —H, halo, alkyl, monoalkylamino, ordialkylamino; R⁵ is —H, alkyl, or halo.
 21. The compound of claim 16 ora pharmaceutically acceptable salt thereof, which is selected from thegroup consisting of:(1S,2S)—N-(6-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-(dimethylamino)-6-fluoro-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-(dimethylamino)-6-fluoro-5-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-(dimethylamino)-6-fluoro-5-(trifluoromethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(isopropylamino)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;and(1S,2S)—N-(6-(5-chloro-6-fluoro-7-isopropyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide.22. The compound of claim 16 or a pharmaceutically acceptable saltthereof, wherein R¹ is cyclopropyl which is optionally substituted withone or more groups selected from the group consisting of halo, C₁₋₃alkyl, C₁₋₃ hydroxyalkyl and C₁₋₃ haloalkyl; R² is —H, alkyl, halo,haloalkyl, or alkylthio; R³ is —H, alkyl, or halo; M is a bond, —O—, —S—or —NR⁶—; R⁴ is —H, halo, alkyl, hydroxyalkyl, haloalkyl, haloalkenyl,cycloalkyl, monoalkylamino, or dialkylamino; and R⁵ is —H, alkyl, orhalo.
 23. The compound of claim 16 or a pharmaceutically acceptable saltthereof, which is selected from the group consisting of:(1S,2S)—N-(6-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-bromo-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(methylamino)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)-2-fluoro-N-(6-(6-fluoro-5-methyl-7-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-methoxy-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-ethoxy-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-(ethylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-ethoxy-6-fluoro-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-(dimethylamino)-5-ethyl-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-ethyl-6-fluoro-7-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)-2-fluoro-N-(6-(6-fluoro-5-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide;(1S,2S)-2-fluoro-N-(6-(6-fluoro-5,7-bis(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-(dimethylamino)-6-fluoro-5-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(6,7-difluoro-5-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-(ethyl(methyl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-ethoxy-6-fluoro-5-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-ethoxy-5-ethyl-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;5-chloro-6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-N,N-dimethyl-1H-indazole-7-carboxamide;(1S,2S)—N-(6-(7-(ethyl(methyl)amino)-6-fluoro-5-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;N-(6-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide;6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-N,N,5-trimethyl-1H-indazole-7-carboxamide;(1S,2S)—N-(6-(7-(ethyl(methyl)amino)-6-fluoro-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1R,2S)—N-(6-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1R,2R)—N-(6-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(2-oxopyrrolidin-1-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;5-chloro-N-ethyl-6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-N-methyl-1H-indazole-7-carboxamide;(1S,2S)-2-fluoro-N-(6-(6-fluoro-5-methyl-7-(trifluoromethoxy)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(methyl(pyridin-3-ylmethyl)amino)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(methyl(pyridin-4-ylmethyl)amino)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(trifluoromethoxy)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(3-methyl-2-oxoimidazolidin-1-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(isopropylamino)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-(cyclopropyl(methyl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-((cyanomethyl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-((1-cyanoethyl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-hydroxyethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-fluoroethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(methoxymethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-(ethoxymethyl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-(1-(2H-tetrazol-2-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-isopropoxy-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-isopropyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-((S)-1-(2H-tetrazol-2-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(2-hydroxycyclopentyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-((S)-1-(1H-tetrazol-1-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-(1-acetamidoethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1,2,2,2-tetrafluoroethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-((R)-1-methoxypropan-2-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-((S)-1-methoxypropan-2-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-((1,1-difluoropropan-2-yl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-formamidoethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-(2,2,2-trifluoroacetamido)ethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;N-(1-(5-chloro-6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-1H-indazol-7-yl)ethyl)cyclobutanecarboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-(methylamino)-1-oxopropan-2-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-((methylthio)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-(methylthio)ethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-(cyano(formamido)methyl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-(1-(2,2-difluoroacetamido)ethyl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;and(1S,2S)—N-(6-(5-chloro-7-(1-(ethylamino)-1-oxopropan-2-yl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide.24. The compound of claim 16 or a pharmaceutically acceptable saltthereof, wherein R¹ is cyclopropyl which is optionally substituted withone or more groups selected from the group consisting of halo, C₁₋₃alkyl, C₁₋₃ hydroxyalkyl and C₁₋₃ haloalkyl; R² is —H, alkyl, halo,haloalkyl, or alkylthio; R³ is —H, alkyl, or halo; M is a bond, —O—, —S—or —NR⁶—; R⁴ is —H, halo, alkyl, alkylcarbonyl, dialkylaminocarbonyl,oxopyrrolidinyl, hydroxyalkyl, haloalkyl, haloalkenyl, cycloalkyl,pyridinyl, monoalkylamino, or dialkylamino; and R⁵ is —H, alkyl, orhalo.
 25. The compound of claim 16 or a pharmaceutically acceptable saltthereof, which is selected from the group consisting of:(1S,2S)—N-(6-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-bromo-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(methylamino)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-bromo-6-fluoro-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)-2-fluoro-N-(6-(6-fluoro-5-methyl-7-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide;(1S,2S)-2-fluoro-N-(6-(6-fluoro-7-methoxy-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-methoxy-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-(dimethylamino)-6-fluoro-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-ethoxy-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-(ethylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-(diethylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-ethoxy-6-fluoro-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-((2-hydroxyethyl)thio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-(dimethylamino)-5-ethyl-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-ethyl-6-fluoro-7-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)-2-fluoro-N-(6-(6-fluoro-5-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide;(1S,2S)-2-fluoro-N-(6-(6-fluoro-5,7-bis(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-ethyl-6,7-difluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-(dimethylamino)-6-fluoro-5-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(6,7-difluoro-5-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-(ethyl(methyl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-(dimethylamino)-6-fluoro-5-(trifluoromethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-ethoxy-6-fluoro-5-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(N-methylacetamido)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-ethoxy-5-ethyl-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;5-chloro-6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-N,N-dimethyl-1H-indazole-7-carboxamide;(1S,2S)—N-(6-(7-(ethyl(methyl)amino)-6-fluoro-5-(methylthio)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-ethyl-7-(ethyl(methyl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;N-(6-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide;6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-N,N,5-trimethyl-1H-indazole-7-carboxamide;(1S,2S)—N-(6-(7-(ethyl(methyl)amino)-6-fluoro-5-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-(difluoromethyl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1R,2S)—N-(6-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2R)—N-(6-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1R,2R)—N-(6-(5-chloro-7-(dimethylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(2-oxopyrrolidin-1-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-ethyl-6-fluoro-7-(trifluoromethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;5-chloro-N-ethyl-6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-N-methyl-1H-indazole-7-carboxamide;(1S,2S)-2-fluoro-N-(6-(6-fluoro-5-methyl-7-(trifluoromethoxy)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)cyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(methyl(pyrimidin-2-yl)amino)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(methyl(pyridin-3-ylmethyl)amino)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(methyl(pyridin-4-ylmethyl)amino)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(trifluoromethoxy)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(3-methyl-2-oxoimidazolidin-1-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(isopropylamino)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-(cyclopropyl(methyl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(hydroxymethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(fluoromethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1H-pyrrol-1-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-((cyanomethyl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-(cyclopropylamino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-(sec-butylamino)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-((1-cyanoethyl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-hydroxyethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-methoxyethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-fluoroethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-methyl-1H-pyrrol-2-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-methyl-1H-pyrazol-5-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-((2H-tetrazol-2-yl)methyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-((2H-1,2,3-triazol-2-yl)methyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(2-methyl-1H-pyrrol-1-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(methoxymethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-(ethoxymethyl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-(1-(2H-tetrazol-2-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-(1-(1H-tetrazol-1-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-cyclopropoxy-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-isopropoxy-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-isopropyl-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-cyclopentyl-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-((S)-1-(2H-tetrazol-2-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(2,2,2-trifluoro-1-hydroxyethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(2-hydroxycyclopentyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-((S)-1-(1H-tetrazol-1-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(2,2,2-trifluoro-1-methoxyethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(7-(1-acetamidoethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1,2,2,2-tetrafluoroethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-((cyclopropylmethyl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-((R)-1-methoxypropan-2-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-((S)-1-methoxypropan-2-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-propionamidoethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-((1,1-difluoropropan-2-yl)amino)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-formamidoethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-(2,2,2-trifluoroacetamido)ethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;N-(1-(5-chloro-6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyridin-6-yl)-1H-indazol-7-yl)ethyl)cyclobutanecarboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-(methylamino)-1-oxopropan-2-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-((methylthio)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-(methylthio)ethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-(cyano(formamido)methyl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;(1S,2S)—N-(6-(5-chloro-7-(1-(2,2-difluoroacetamido)ethyl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide;and(1S,2S)—N-(6-(5-chloro-7-(1-(ethylamino)-1-oxopropan-2-yl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyridin-2-yl)-2-fluorocyclopropane-1-carboxamide.26. The compound of claim 1 or a pharmaceutically acceptable saltthereof, which is a compound of Formula (VI):


27. (canceled)
 28. (canceled)
 29. (canceled)
 30. A pharmaceuticalcomposition comprising a pharmaceutically acceptable carrier or diluentand the compound of claim 1 or a pharmaceutically acceptable saltthereof.
 31. A method of treating a subject with a disease or disorderassociated with modulation of HPK1 comprising: administering to thesubject in need thereof a therapeutically effective amount of thecompound of claim 1 or a pharmaceutically acceptable salt thereof. 32.(canceled)
 33. (canceled)
 34. (canceled)